Pyridine compound

ABSTRACT

A pyridine compound represented by formula (I), or an N-oxide thereof is provided, wherein the variable groups are as defined in the specification. The pyridine compound of formula has excellent control effects against harmful arthropods.

TECHNICAL FIELD

The present invention relates to a certain class of pyridine compoundand its use for controlling harmful arthropods.

BACKGROUND ART

To date, some compounds for controlling harmful arthropods have beendeveloped and come into practical use.

Also, a certain class of heterocyclic compounds has been known (forexample, see Patent Document 1).

CITATION LIST Patent Document

Patent Document 1: JP 2000-26421 A

SUMMARY OF THE INVENTION Problems to be Solved by Invention

An object of the present invention is to provide a compound havingexcellent control efficacies against harmful arthropods.

Means to Solve Problems

The present invention provides the followings.

[1] A compound represented by formula (I)

[wherein:

R¹ represents a C2-C10 chain hydrocarbon group having one or morehalogen atoms, a (C1-C5 alkoxy)C2-C5 alkyl group having one or morehalogen atoms, a (C1-C5 alkylsulfanyl)C2-C5 alkyl group having one ormore halogen atoms, a (C1-C5 alkylsulfinyl)C2-C5 alkyl group having oneor more halogen atoms, a (C1-C5 alkylsulfonyl)C2-C5 alkyl group havingone or more halogen atoms, a (C3-C7 cycloalkyl)C1-C3 alkyl group havingone or more substituents selected from Group G, or a C3-C7 cycloalkylgroup having one or more substituents selected from Group G;

R² represents a C1-C6 alkyl group optionally having one or more halogenatoms, a cyclopropylmethyl group, or a cyclopropyl group;

q represents 0, 1, 2, 3, or 4;

R³ represents a C1-C6 chain hydrocarbon group optionally having one ormore substituents selected from Group B, a phenyl group optionallyhaving one or more substituents selected from Group D, a 5 or 6 memberedaromatic heterocyclic group optionally having one or more substituentsselected from Group D, a OR¹², a NR¹¹R¹², a NR^(11a)R^(12a), aNR²⁹NR¹¹R¹², a NR²⁹OR¹¹, a NR¹¹C(O)R¹³, a NR²⁹NR¹¹C(O)R¹³, aNR¹¹C(O)OR¹⁴, a NR²⁹NR¹¹C(O)OR¹⁴, a NR¹¹C(O)NR¹⁵R¹⁶, aNR²⁴NR¹¹C(O)NR¹⁵R¹⁶, a N═CHNR¹⁵R¹⁶, a N═S(O)_(x)R¹⁵R¹⁶, a S(O)_(y)R¹⁵, aSF₅, a C(O)OR¹⁷, a C(O)NR¹¹R¹², a cyano group, a nitro group, or ahalogen atom, wherein when q represents 2 or 3, two or three R³ may beidentical to or different from each other;

p represents 0, 1, 2, or 3;

R⁶ represents a C1-C6 alkyl group optionally having one or more halogenatoms, a OR¹⁸, a NR¹⁸R¹⁹, a cyano group, a nitro group, or a halogenatom, wherein when p represents 2, two R⁶ may be identical to ordifferent from each other;

R¹¹, R¹⁷, R¹⁸, R¹⁹, R²⁴, and R²⁹ represent each independently a hydrogenatom or a C1-C6 chain hydrocarbon group optionally having one or morehalogen atoms;

R¹² represents a hydrogen atom, a C1-C6 chain hydrocarbon groupoptionally having one or more halogen atoms, a C1-C6 alkyl group havingone substituent selected from Group F, or a S(O)₂R²³;

R²³ represents a C1-C6 chain hydrocarbon group optionally having one ormore halogen atoms or a phenyl group optionally having one or moresubstituents selected from Group D;

R^(11a) and R^(12a) are combined with the nitrogen atom to which theyare attached to represent a 3-7 membered nonaromatic heterocyclic groupoptionally having one or more substituents selected from Group E{wherein said 3-7 membered nonaromatic heterocyclic group represents anaziridine ring, an azetidine ring, a pyrrolidine ring, an imidazolinering, an imidazolidine ring, a piperidine ring, a tetrahydropyrimidinering, a hexahydropyrimidine ring, a piperazine ring, an azepane ring, anoxazolidine ring, an isoxazolidine ring, a 1,3-oxazinane ring, amorpholine ring, a 1,4-oxazepane ring, a thiazolidine ring, anisothiazolidine ring, a 1,3-thiazinane ring, a thiomorpholine ring, or a1,4-thiazepane ring};

R¹³ represents a hydrogen atom, a C1-C6 chain hydrocarbon groupoptionally having one or more halogen atoms, a C3-C7 cycloalkyl groupoptionally having one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3alkyl group optionally having one or more halogen atoms, a phenyl groupoptionally having one or more substituents selected from Group D, or a 5or 6 membered aromatic heterocyclic group optionally having one or moresubstituents selected from Group D;

R¹⁴ represents a C1-C6 chain hydrocarbon group optionally having one ormore halogen atoms, a C3-C7 cycloalkyl group optionally having one ormore halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group optionallyhaving one or more halogen atoms, or a phenyl C1-C3 alkyl group {whereinthe phenyl moiety in the phenyl C1-C3 alkyl group may optionally haveone or more substituents selected from Group D};

R¹⁵ and R¹⁶ represent each independently a C1-C6 alkyl group optionallyhaving one or more halogen atoms;

n and y represent each independently 0, 1, or 2;

x represents 0 or 1;

Group B: a group consisting of a C1-C6 alkoxy group optionally havingone or more halogen atoms, a C3-C6 alkenyloxy group optionally havingone or more halogen atoms, a C3-C6 alkynyloxy group optionally havingone or more halogen atoms, a C1-C6 alkylsulfanyl group optionally havingone or more halogen atoms, a C1-C6 alkylsulfinyl group optionally havingone or more halogen atoms, a C1-C6 alkylsulfonyl group optionally havingone or more halogen atoms, a C3-C6 cycloalkyl group optionally havingone or more halogen atoms, a cyano group, a hydroxy group, and a halogenatom;

Group C: a group consisting of a C1-C6 chain hydrocarbon groupoptionally having one or more halogen atoms, a C1-C6 alkoxy groupoptionally having one or more halogen atoms, a C3-C6 alkenyloxy groupoptionally having one or more halogen atoms, a C3-C6 alkynyloxy groupoptionally having one or more halogen atoms, and a halogen atom;

Group D: a group consisting of a C1-C6 chain hydrocarbon groupoptionally having one or more halogen atoms, a hydroxy group, a C1-C6alkoxy group optionally having one or more halogen atoms, a C3-C6alkenyloxy group optionally having one or more halogen atoms, a C3-C6alkynyloxy group optionally having one or more halogen atoms, a sulfanylgroup, a C1-C6 alkylsulfanyl group optionally having one or more halogenatoms, a C1-C6 alkylsulfinyl group optionally having one or more halogenatoms, a C1-C6 alkylsulfonyl group optionally having one or more halogenatoms, an amino group, a NHR²¹, a NR²¹R²², a C(O)R²¹ group, a OC(O)R²¹group, a C(O)OR²¹ group, a cyano group, a nitro group, and a halogenatom {wherein R²¹ and R²² represent each independently a C1-C6 alkylgroup optionally having one or more halogen atoms};

Group E: a group consisting of a C1-C6 chain hydrocarbon groupoptionally having one or more halogen atoms, a C1-C6 alkoxy groupoptionally having one or more halogen atoms, a C3-C6 alkenyloxy groupoptionally having one or more halogen atoms, a C3-C6 alkynyloxy groupoptionally having one or more halogen atoms, a halogen atom, an oxogroup, a hydroxy group, a cyano group, and a nitro group;

Group F: a group consisting of a C1-C6 alkoxy group optionally havingone or more halogen atoms, an amino group, a NHR²¹, a NR²¹R²², a cyanogroup, a phenyl group optionally having one or more substituentsselected from Group D, a 5 or 6 membered aromatic heterocyclic groupoptionally having one or more substituents selected from Group D, aC3-C7 cycloalkyl group optionally having one or more halogen atoms, anda 3-7 membered nonaromatic heterocyclic group optionally having one ormore substituents selected from Group C;

Group G: a group consisting of a halogen atom and a C1-C6 haloalkylgroup]

or an N-oxide compound thereof (hereinafter a compound represented byformula (I) or an N-oxide compound thereof is referred to as “compoundof the present invention” or “Present compound”).[2] The compound according to [1], wherein

q represents 0, 1, or 2; and

R³ represents a C1-C6 chain hydrocarbon group optionally having one ormore substituents selected from Group B, a phenyl group optionallyhaving one or more substituents selected from Group D, a 5 or 6 memberedaromatic heterocyclic group optionally having one or more substituentsselected from Group D, a OR¹², a NR¹¹R¹², a NR^(11a)R^(12a), aNR¹¹C(O)R¹³, a NR²⁹NR¹¹C(O)R¹³, a NR¹¹C(O)OR¹⁴, a C(O)OR¹⁷, aC(O)NR¹¹R¹², a cyano group, a nitro group, or a halogen atom.

[3] The compound according to [1], wherein

q represents 0, 1, or 2;

R³ represents a C1-C6 alkyl group having one or more halogen atoms, aOR¹², or a halogen atom; and

R¹² represents a hydrogen atom or a C1-C3 alkyl group optionally havingone or more halogen atoms.

[4] The compound according to any one of [1] to [3], wherein

p represents 0 or 1; and

R⁶ represents a C1-C6 alkyl group optionally having one or more halogenatoms, or a halogen atom.

[5] The compound according to any one of [1] to [3], wherein prepresents 0.[6] The compound according to any one of [1] to [5], wherein R¹represents a C2-C10 haloalkyl group.[7] The compound according to any one of [1] to [5], wherein R¹represents a C3-C5 alkyl group having four or more fluorine atoms.[8] The compound according to any one of [1] to [7], wherein R²represents a C1-C6 alkyl group optionally having one or more halogenatoms.[9] The compound according to any one of [1] to [7], wherein R²represents an ethyl group.[10] The compound according to [1], wherein

R¹ represents a C2-C10 haloalkyl group;

R² represents an ethyl group;

q represents 0 or 1;

R³ represents a C1-C6 alkyl group optionally having one or more halogenatoms, or a halogen atom;

p represents 0 or 1; and

R⁶ represents a C1-C6 alkyl group optionally having one or more halogenatoms, or a halogen atom.

[11] The compound according to [1], wherein

R¹ represents a C3-C5 alkyl group having four or more fluorine atoms;

-   -   R² represents an ethyl group;    -   q represents 0 or 1;    -   R³ represents a C1-C6 alkyl group optionally having one or more        halogen atoms, or a halogen atom; and

p represents 0.

[12] A composition for controlling a harmful arthropod comprising thecompound according to any one of [1] to [11] and an inert carrier.[13] A method for controlling a harmful arthropod which comprisesapplying an effective amount of the compound according to any one of [1]to [11] to a harmful arthropod or a habitat where a harmful arthropodlives.

Effect of Invention

The Present compound has excellent control efficacies against harmfularthropods, and thus is useful as an active ingredient of an agent forcontrolling harmful arthropods.

MODE FOR CARRYING OUT THE INVENTION

The substituent(s) in the present invention is/are explained as follows.

When a substituent “optionally having one or more halogen atoms” has twoor more halogen atoms, these halogen atoms may be identical to ordifferent from each other.

The expression of “CX-CY” as described herein means that the number ofcarbon atom is X to Y. For example, the expression of “C1-C6” means thatthe number of carbon atom is 1 to 6.

The term of “halogen atom” represents fluorine atom, chlorine atom,bromine atom, or iodine atom.

The term of “chain hydrocarbon group” represents an alkyl group, analkenyl group, and an alkynyl group.

Examples of the term of “alkyl group” include methyl group, ethyl group,propyl group, isopropyl group, 1,1-dimethylpropyl group,1,2-dimethylpropyl group, 1-ethylpropyl group, butyl group, tert-butylgroup, pentyl group, and hexyl group.

Examples of the term of “alkenyl group” include vinyl group, 1-propenylgroup, 2-propenyl group, 1-methyl-1-propenyl group, 1-methyl-2-propenylgroup, 1,2-dimethyl-1-propenyl group, 1,1-dimethyl-2-propenyl group,1-ethyl-1-propenyl group, 1-ethyl-2-propenyl group, 3-butenyl group,4-pentenyl group, and 5-hexenyl group.

Examples of the term of “alkynyl group” include ethynyl group,1-propynyl group, 2-propynyl group, 1-methyl-2-propynyl group,1,1-dimethyl-2-propynyl group, 1-ethyl-2-propynyl group, 2-butynylgroup, 4-pentynyl group, and 5-hexynyl group.

The term of “C2-C10 haloalkyl group” represents a C2-C10 alkyl groupwherein one or more hydrogen atoms are substituted with one or morehalogen atoms, and examples thereof include a C2-C10 fluoroalkyl group.

Examples of the term of “C2-C10 haloalkyl group” include chloroethylgroup, 2,2,2-trifluoroethyl group, 2-bromo-1,1,2,2-tetrafluoroethylgroup, 2,2,3,3-tetrafluoropropyl group,1-methyl-2,2,3,3-tetrafluoropropyl group, perfluorohexyl group, andperfluorodecyl group.

Examples of the term of “C2-C10 fluoroalkyl group” include2,2,2-trifluoroethyl group, 2,2,3,3-tetrafluoropropyl group,1-methyl-2,2,3,3-tetrafluoropropyl group, perfluorohexyl group, andperfluorodecyl group.

Examples of the term of “cycloalkyl group” include cyclopropyl group,cyclobutyl group, cyclopentyl group, cyclohexyl group, and cycloheptylgroup.

The term of “3-7 membered nonaromatic heterocyclic group” represents anaziridine ring, an azetidine ring, a pyrrolidine ring, an imidazolinering, an imidazolidine ring, a piperidine ring, a tetrahydropyrimidinering, a hexahydropyrimidine ring, a piperazine ring, an azepane ring, anoxazolidine ring, an isoxazolidine ring, a 1,3-oxazinane ring, amorpholine ring, a 1,4-oxazepane ring, a thiazolidine ring, anisothiazolidine ring, a 1,3-thiazinane ring, a thiomorpholine ring, or a1,4-thiazepane ring, and examples of “3-7 membered nonaromaticheterocyclic group optionally having one or more substituents selectedfrom Group E” include the following groups.

Examples of the term of “phenyl C1-C3 alkyl group {wherein the phenylmoiety in the phenyl C1-C3 alkyl group may optionally have one or moresubstituents selected from Group D}” include benzyl group,2-fluorobenzyl group, 4-chlorobenzyl group, 4-(trifluoromethyl)benzylgroup, and 2-[4-(trifluoromethyl)phenyl]ethyl group.

The term of “(C1-C5 alkoxy)C2-C5 alkyl group having one or more halogenatoms” represents a group wherein the (C1-C5 alkoxy) and/or the (C2-C5alkyl) has one or more halogen atoms, and examples thereof include2-(trifluoromethoxy)ethyl group, 2,2-difluoro-3-methoxypropyl group,2,2-difluoro-3-(2,2,2-trifluoroethoxy)propyl group, and3-(2-chloroethoxy)propyl group.

The term of “(C1-C5 alkylsulfanyl)C2-C5 alkyl group having one or morehalogen atoms” represents a group wherein the (C1-C5 alkylsulfanyl)and/or the (C2-C5 alkyl) has one or more halogen atoms, and examplesthereof include 2,2-difluoro-2-(trifluoromethylthio)ethyl group.

The term of “(C1-C5 alkylsulfinyl)C2-C5 alkyl group having one or morehalogen atoms” represents a group wherein the (C1-C5 alkylsulfinyl)and/or the (C2-C5 alkyl) has one or more halogen atoms, and examplesthereof include 2,2-difluoro-2-(trifluoromethanesulfinyl)ethyl group.

The term of “(C1-C5 alkylsulfonyl)C2-C5 alkyl group having one or morehalogen atoms” represents a group wherein the (C1-C5 alkylsulfonyl)and/or the (C2-C5 alkyl) has one or more halogen atoms, and examplesthereof include 2,2-difluoro-2-(trifluoromethanesulfonyl)ethyl group.

The term of “(C3-C6 cycloalkyl)C1-C3 alkyl group optionally having oneor more halogen atoms” represents a group wherein the (C3-C6 cycloalkyl)and/or the (C1-C3 alkyl) may optionally have one or more halogen atoms,and examples thereof include (2,2-difluorocyclopropyl)methyl group,2-cyclopropyl-1,1,2,2-tetrafluoroethyl group, and2-(2,2-difluorocyclopropyl)-1,1,2,2-tetrafluoroethyl group.

The term of “(C3-C7 cycloalkyl)C1-C3 alkyl group having one or moresubstituents selected from Group G” represents a group wherein the(C3-C7 cycloalkyl) and/or the (C1-C3 alkyl) has one or more substituentsselected from Group G, and examples thereof include(2,2-difluorocyclopropyl)methyl group,[1-(trifluoromethyl)cyclopropyl]methyl group,[2-(trifluoromethyl)cyclopropyl]methyl group,2-cyclopropyl-1,1,2,2-tetrafluoroethyl group,2-cyclopropyl-3,3,3,3-trifluoropropyl group, and1,1,2,2-tetrafluoro-2-[2-(trifluoromethyl)cyclopropyl]ethyl group.

Examples of the term of “C3-C7 cycloalkyl group having one or moresubstituents selected from Group G” include 2,2-difluorocyclopropylgroup, 1-(2,2,2-trifluoroethyl)cyclopropyl group, and4-(trifluoromethyl)cyclohexyl group.

The term of “5 or 6 membered aromatic heterocyclic group” represents a 5membered aromatic heterocyclic group or a 6 membered aromaticheterocyclic group, and the term of “5 membered aromatic heterocyclicgroup” represents pyrrolyl group, furyl group, thienyl group, pyrazolylgroup, imidazolyl group, triazolyl group, tetrazolyl group, oxazolylgroup, isoxazolyl group, thiazolyl group, oxadiazolyl group, orthiadiazolyl group, and the term of “6 membered aromatic heterocyclicgroup” represents pyridyl group, pyridazinyl group, pyrimidinyl group,or pyrazinyl group.

The term of “5 membered aromatic heterocyclic group comprising 1 to 4nitrogen atoms” represents pyrrolyl group, pyrazolyl group, imidazolylgroup, 1,2,4-triazolyl group, 1,2,3-triazolyl group, or tetrazolylgroup.

The term of “N-oxide compound” represents a compound represented by thefollowing formula (I-N1).

[wherein the symbols are the same as defined above.]

Embodiments of the Present compound include the following compounds.

The Present compound, wherein R¹ represents a C2-C10 haloalkyl group ora (C3-C7 cycloalkyl)C1-C3 alkyl group having one or more substituentsselected from Group G;

The Present compound, wherein R¹ represents a C2-C10 haloalkyl group;

The Present compound, wherein R¹ represents a C2-C10 alkyl group havingtwo or more fluorine atoms;

The Present compound, wherein R¹ represents a C2-C6 alkyl group havingfour or more fluorine atoms;

The Present compound, wherein R² represents a C1-C6 alkyl groupoptionally having one or more halogen atoms;

The Present compound, wherein R² represents a C1-C6 alkyl group;

The Present compound, wherein R² represents a C2-C6 alkyl group;

The Present compound, wherein R² represents a methyl group or an ethylgroup;

The Present compound, wherein R² represents an ethyl group;

The Present compound, wherein q represents 0, 1, 2, or 3, and R³represents a C1-C6 chain hydrocarbon group optionally having one or moresubstituents selected from Group B, a phenyl group optionally having oneor more substituents selected from Group D, a 5 or 6 membered aromaticheterocyclic group optionally having one or more substituents selectedfrom Group D, a OR¹², a NR¹¹R¹², a NR^(11a)R^(12a), a S(O)_(y)R¹⁵, or ahalogen atom;

The Present compound, wherein q represents 0, 1, or 2, and R³ representseach independently a C1-C6 chain hydrocarbon group optionally having oneor more halogen atoms, a phenyl group optionally having one or moresubstituents selected from Group D, a 6 membered aromatic heterocyclicgroup comprising 1 to 2 nitrogen atoms (wherein said 6 membered aromaticheterocyclic group may optionally have one or more substituents selectedfrom Group D), a 5 membered aromatic heterocyclic group comprising 1 to4 nitrogen atoms (wherein said 5 membered aromatic heterocyclic groupmay optionally have one or more substituents selected from Group D), aOR¹², a NR¹¹R¹², a NR²⁹NR¹¹R¹², a S(O)_(y)R¹⁵, or a halogen atom;

The Present compound, wherein q represents 0, 1, or 2, and R³ representseach independently a C1-C6 chain hydrocarbon group optionally having oneor more substituents selected from Group B, a phenyl group optionallyhaving one or more substituents selected from Group D, a 6 memberedaromatic heterocyclic group selected from Group R (wherein said 6membered aromatic heterocyclic group may optionally have one or moresubstituents selected from Group D), a 5 membered aromatic heterocyclicgroup selected from Group Q (wherein said 5 membered aromaticheterocyclic group may optionally have one or more substituents selectedfrom Group D), a OR¹², a NR¹¹R¹², a NR^(11a)R^(12a), a NR²⁹NR¹¹R¹², aS(O)_(y)R¹⁵, or a halogen atom;

The Present compound, wherein q represents 0, 1, or 2, and R³ representseach independently a C1-C6 chain hydrocarbon group optionally having oneor more substituents selected from Group B, a 6 membered aromaticheterocyclic group selected from Group R (wherein said 6 memberedaromatic heterocyclic group may optionally have one or more substituentsselected from Group D), a 5 membered aromatic heterocyclic groupselected from Group Q (wherein said 5 membered aromatic heterocyclicgroup may optionally have one or more substituents selected from GroupD), a OR¹², a NR¹¹R¹², a NR^(11a)R^(12a), a NR²⁹NR¹¹R¹², a S(O)_(y)R¹⁵,or a halogen atom;

Group R:

The Present compound, wherein q represents 0, 1, or 2, and R³ representsa C1-C6 chain hydrocarbon group optionally having one or moresubstituents selected from Group B, a 5 membered aromatic heterocyclicgroup selected from Group Q (wherein said 5 membered aromaticheterocyclic group may optionally have one or more substituents selectedfrom Group D), a OR¹², a NR¹¹R¹², a NR^(11a)R^(12a), a NR²⁹NR¹¹R¹², aS(O)_(y)R¹⁵, or a halogen atom;

Group Q:

{wherein R²⁶ represents a C1-C6 alkyl group optionally having one ormore halogen atoms.}

The Present compound, wherein q represents 0, 1, or 2, and R³ representsa C1-C6 chain hydrocarbon group optionally having one or more halogenatoms, a 5 membered aromatic heterocyclic group comprising 1 to 4nitrogen atoms (wherein said 5 membered aromatic heterocyclic group mayoptionally have one or more substituents selected from Group D), a OR¹²,a NR¹¹R¹², a NR²⁹NR¹¹R¹², a S(O)_(y)R¹⁵, or a halogen atom;

The Present compound, wherein q represents 0 or 1, and R³ represents aC1-C6 alkyl group optionally having one or more halogen atoms, a OR¹²,or a halogen atom;

The Present compound, wherein q represents 0 or 1, and R³ represents aC1-C6 alkyl group optionally having one or more halogen atoms, or ahalogen atom;

The Present compound, wherein R⁶ represents a C1-C6 alkyl groupoptionally having one or more halogen atoms, or a halogen atom;

The Present compound, wherein p represents 0 or 1, and R⁶ represents aC1-C6 alkyl group optionally having one or more halogen atoms, or ahalogen atom;

The Present compound, wherein p represents 0;

The Present compound, wherein R¹ represents a C2-C10 haloalkyl group,

R² represents a C1-C6 alkyl group optionally having one or more halogenatoms,q represents 0, 1, 2, or 3, R³ represents a C1-C6 chain hydrocarbongroup optionally having one or more substituents selected from Group B,a 5 membered aromatic heterocyclic group selected from Group Q (whereinsaid 5 membered aromatic heterocyclic group may optionally have one ormore substituents selected from Group D), a OR¹², a NR¹¹R¹², aNR^(11a)R^(12a), a NR²⁹NR¹¹R¹², a S(O)_(y)R¹⁵, or a halogen atom,p represents 0 or 1, and R⁶ represents a C1-C6 alkyl group optionallyhaving one or more halogen atoms, or a halogen atom;

The Present compound, wherein R¹ represents a C2-C10 haloalkyl group,

R² represents an ethyl group,q represents 0, 1, 2, or 3, R³ represents each independently a C1-C6chain hydrocarbon group optionally having one or more halogen atoms, aphenyl group optionally having one or more substituents selected fromGroup D, a 6 membered aromatic heterocyclic group comprising 1 to 2nitrogen atoms (wherein said 6 membered aromatic heterocyclic group mayoptionally have one or more substituents selected from Group D), a 5membered aromatic heterocyclic group comprising 1 to 4 nitrogen atoms(wherein said 5 membered aromatic heterocyclic group may optionally haveone or more substituents selected from Group D) a OR¹², a NR¹¹R¹², aNR²⁹NR¹¹R¹², a S(O)_(y)R¹⁵, or a halogen atom,R¹¹ and R¹² represent each independently a hydrogen atom or a C1-C3alkyl group optionally having one or more halogen atoms,R¹⁵ represents a C1-C3 alkyl group optionally having one or more halogenatoms,p represents 0 or 1, and R⁶ represents a C1-C6 alkyl group optionallyhaving one or more halogen atoms, or a halogen atom;

The Present compound, wherein R¹ represents a C2-C10 haloalkyl group,

R² represents an ethyl group,q represents 0, 1, 2, or 3, R³ represents each independently a C1-C6chain hydrocarbon group optionally having one or more substituentsselected from Group B, a 6 membered aromatic heterocyclic group selectedfrom Group R (wherein said 6 membered aromatic heterocyclic group mayoptionally have one or more substituents selected from Group D), a 5membered aromatic heterocyclic group selected from Group Q (wherein said5 membered aromatic heterocyclic group may optionally have one or moresubstituents selected from Group D), a OR¹², a NR¹¹R¹², aNR^(11a)R^(12a), a NR²⁹NR¹¹R¹², a S(O)_(y)R¹⁵, or a halogen atom,R¹¹ and R¹² represent each independently a hydrogen atom or a C1-C3alkyl group optionally having one or more halogen atoms,R¹⁵ represents a C1-C3 alkyl group optionally having one or more halogenatoms,p represents 0 or 1, and R⁶ represents a C1-C6 alkyl group optionallyhaving one or more halogen atoms, or a halogen atom;

The Present compound, wherein R¹ represents a C2-C10 haloalkyl group,

R² represents an ethyl group,q represents 0, 1, 2, or 3, R³ represents a C1-C6 chain hydrocarbongroup optionally having one or more halogen atoms, a 5 membered aromaticheterocyclic group comprising 1 to 4 nitrogen atoms (wherein said 5membered aromatic heterocyclic group may optionally have one or moresubstituents selected from Group D), a OR¹², a NR¹¹R¹², a NR²⁹NR¹¹R¹², aS(O)_(y)R¹⁵, or a halogen atom,R¹¹ and R¹² represent each independently a hydrogen atom or a C1-C3alkyl group optionally having one or more halogen atoms,R¹⁵ represents a C1-C3 alkyl group optionally having one or more halogenatoms,p represents 0 or 1, and R⁶ represents a C1-C6 alkyl group optionallyhaving one or more halogen atoms, or a halogen atom;

The Present compound, wherein R¹ represents a C2-C10 alkyl group havingtwo or more fluorine atoms,

R² represents an ethyl group,q represents 0, 1, 2, or 3, R³ represents a C1-C6 alkyl group optionallyhaving one or more halogen atoms, a OR¹², or a halogen atom,R¹² represents a hydrogen atom or a C1-C3 alkyl group optionally havingone or more halogen atoms, andp represents 0;

The Present compound, wherein R¹ represents a C3-C6 alkyl group havingfour or more fluorine atoms,

R² represents an ethyl group,q represents 0, 1, 2, or 3, R³ represents a C1-C6 alkyl group optionallyhaving one or more halogen atoms, a 5 membered aromatic heterocyclicgroup selected from Group Q (wherein said 5 membered aromaticheterocyclic group may optionally have one or more substituents selectedfrom Group D), a OR¹², a NR¹¹R¹², a NR^(11a)R^(12a), a S(O)_(y)R¹⁵, or ahalogen atom,R¹¹ and R¹² represent each independently a hydrogen atom or a C1-C3alkyl group optionally having one or more halogen atoms,R¹⁵ represents a C1-C3 alkyl group optionally having one or more halogenatoms,p represents 0 or 1, and R⁶ represents a C1-C6 alkyl group optionallyhaving one or more halogen atoms, or a halogen atom;

The Present compound, wherein R¹ represents a C3-C6 haloalkyl grouphaving four or more fluorine atoms,

R² represents an ethyl group,q represents 0, 1, 2, or 3, R³ represents a C1-C6 alkyl group optionallyhaving one or more halogen atoms, a OR¹², or a halogen atom,R¹² represents a hydrogen atom or a C1-C3 alkyl group optionally havingone or more halogen atoms, andp represents 0;

The compound represented by formula (I), wherein R¹ represents a C2-C10haloalkyl group, R² represents a C1-C6 alkyl group, q represents 0 or 1,R³ represents a C1-C6 alkyl group optionally having one or more halogenatoms, a OR¹², or a halogen atom, R¹² represents a C1-C6 alkyl groupoptionally having one or more halogen atoms, and p represents 0.

The compound represented by formula (I), wherein R¹ represents a C2-C10alkyl group having one or more halogen atoms, a C3-C10 alkenyl grouphaving one or more halogen atoms, a (C1-C5 alkoxy)C2-C5 alkyl grouphaving one or more halogen atoms, a (C1-C5 alkylsulfanyl)C2-C5 alkylgroup having one or more halogen atoms, a (C1-C5 alkylsulfinyl)C2-C5alkyl group having one or more halogen atoms, a (C1-C5alkylsulfonyl)C2-C5 alkyl group having one or more halogen atoms, or a(C3-C7 cycloalkyl)C1-C3 alkyl group having one or more halogen atoms, R²represents a C1-C6 alkyl group, q represents 0 or 1, R³ represents aC1-C6 alkyl group optionally having one or more halogen atoms, a OR¹², aS(O)_(y)R¹⁵, a pyridyl group, a pyridazinyl group, a pyrimidinyl group,a pyrazinyl group, or a halogen atom, R¹² and R¹⁵ represent eachindependently a C1-C6 alkyl group optionally having one or more halogenatoms, and p represents 0.

Next, a process for preparing the Present compound is described.

The Present compound may be prepared, for example, according to thefollowing processes.

Process 1

A compound represented by formula (Ib) (hereinafter referred to as“Present compound (Ib)”) and a compound represented by formula (Ic)(hereinafter referred to as “Present compound (Ic)”) may be prepared byreacting a compound represented by formula (Ia) (hereinafter referred toas “Present compound (Ia)”) with an oxidizing agent.

[wherein the symbols are the same as defined above.]

First, a process for preparing the Present compound (Ib) from thePresent compound (Ia) is described.

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include aliphatic halogenatedhydrocarbons such as dichloromethane and chloroform (hereinaftercollectively referred to as “aliphatic halogenated hydrocarbons”);nitriles such as acetonitrile (hereinafter collectively referred to as“nitriles”); esters such as ethyl acetate; alcohols such as methanol andethanol (hereinafter collectively referred to as “alcohols”); aceticacid; water; and mixed solvents thereof.

Examples of the oxidizing agent to be used in the reaction includesodium periodate, m-chloroperbenzoic acid (hereinafter referred to as“mCPBA”), and hydrogen peroxide.

When hydrogen peroxide is used as the oxidizing agent, sodium carbonateor a catalyst may be added to the reaction as needed.

Examples of the catalyst to be used in the reaction include tungsticacid and sodium tungstate.

In the reaction, the oxidizing agent is usually used within a range of 1to 1.2 molar ratio(s), the base is usually used within a range of 0.01to 1 molar ratio(s), and the catalyst is usually used within a range of0.01 to 0.5 molar ratios, relative to 1 mole of the Present compound(Ia).

The reaction temperature of the reaction is usually within a range of−20 to 80° C. The reaction period of the reaction is usually within arange of 0.1 to 12 hours.

When the reaction is completed, the reaction mixture is extracted withorganic solvent(s), and the organic layers are sequentially washed withan aqueous solution of a reducing agent (for example, sodium sulfite orsodium thiosulfate) and an aqueous solution of a base (for example,sodium hydrogen carbonate) as needed. The resulting organic layers aredried and concentrated to give the Present compound (Ib).

Next, a process for preparing the Present compound (Ic) from the Presentcompound (Ib) is described.

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include aliphatic halogenatedhydrocarbons, nitriles, alcohols, acetic acid, water, and mixed solventsthereof.

Examples of the oxidizing agent to be used in the reaction include mCPBAand hydrogen peroxide.

When hydrogen peroxide is used as the oxidizing agent, a base or acatalyst may be added to the reaction as needed.

Examples of the base to be used in the reaction include sodiumcarbonate.

Examples of the catalyst to be used in the reaction include sodiumtungstate.

In the reaction, the oxidizing agent is usually used within a range of 1to 2 molar ratio(s), the base is usually used within a range of 0.01 to1 molar ratio(s), and the catalyst is usually used within a range of0.01 to 0.5 molar ratios, relative to 1 mole of the Present compound(Ib).

The reaction temperature of the reaction is usually within a range of−20 to 120° C. The reaction period of the reaction is usually within arange of 0.1 to 12 hours.

When the reaction is completed, the reaction mixture is extracted withorganic solvent(s), and the organic layers are sequentially washed withan aqueous solution of a reducing agent (for example, sodium sulfite orsodium thiosulfate) and an aqueous solution of a base (for example,sodium hydrogen carbonate) as needed. The organic layers are dried andconcentrated to give the Present compound (Ic).

Also, the Present compound (Ic) may be prepared in one step reaction(one-pot) by reacting the Present compound (Ia) with an oxidizing agent.

The reaction may be carried out by using the oxidizing agent usually at2.0 to 2.4 molar ratios relative to 1 mole of the Present compound (Ia)according to the process for preparing the Present compound (Ic) fromthe Present compound (Ib)

Process 2

The Present compound represented by formula (I) (hereinafter referred toas “Present compound (I)”) may be prepared by reacting a compoundrepresented by formula (M-3) (hereinafter referred to as “Compound(M-3)”) with a compound represented by formula (R-3) (hereinafterreferred to as “Compound (R-3)”) in the presence of a base.

[wherein: V¹ represents a halogen atom, a C1-C10perfluoroalkanesulfonyloxy group, or a tosyloxy group; and the othersymbols are the same as defined above.]

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include ethers such astetrahydrofuran, ethylene glycol dimethyl ether, methyl-tert-butyl ether(hereinafter referred to as “MTBE”), and 1,4-dioxane (hereinaftercollectively referred to as “ethers”); aliphatic halogenatedhydrocarbons; aromatic hydrocarbons such as toluene and xylene(hereinafter collectively referred to as “aromatic hydrocarbons”);aprotic polar solvents such as dimethylformamide (hereinafter referredto as “DMF”), N-methylpyrrolidone (hereinafter referred to as “NMP”),and dimethyl sulfoxide (hereinafter referred to as “DMSO”) (hereinaftercollectively referred to as “aprotic polar solvents”); and mixedsolvents thereof.

Examples of the base to be used in the reaction include organic basessuch as triethylamine, diisopropylethylamine, pyridine, and4-(dimethylamino)pyridine (hereinafter collectively referred to as“organic bases”); alkali metal hydrides such as sodium hydride(hereinafter collectively referred to as “alkali metal hydrides”); andalkali metal carbonates such as sodium carbonate and potassium carbonate(hereinafter collectively referred to as “alkali metal carbonates”).

In the reaction, the Compound (R-3) is usually used within a range of 1to 10 molar ratio(s), and the base is usually used within a range of 0.1to 5 molar ratios, relative to 1 mole of the Compound (M-3).

The reaction temperature of the reaction is usually within a range of−20° C. to 120° C. The reaction period of the reaction is usually withina range of 0.1 to 24 hours.

When the reaction is completed, the reaction mixture is extracted withorganic solvent(s), and the organic layers are worked up (for example,dried or concentrated) to give the Present compound (I).

Process 3

The Present compound (Ia) may be prepared by reacting a compoundrepresented by formula (M-1) (hereinafter referred to as “Compound(M-1)”) with a compound represented by formula (R-1) (hereinafterreferred to as “Compound (R-1)”) in the presence of a base.

[wherein: V represents a halogen atom; and the other symbols are thesame as defined above.]

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include ethers, aromatichydrocarbons, nitriles, aprotic polar solvents, and mixed solventsthereof.

Examples of the base to be used in the reaction include alkali metalcarbonates and alkali metal hydrides.

In the reaction, the Compound (R-1) is usually used within a range of 1to 10 molar ratio(s), and the base is usually used within a range of 1to 10 molar ratio(s), relative to 1 mole of the Compound (M-1).

The reaction temperature of the reaction is usually within a range of−20° C. to 150° C. The reaction period of the reaction is usually withina range of 0.5 to 24 hours.

When the reaction is completed, the reaction mixture is extracted withorganic solvent(s), and the organic layers are worked up (for example,dried or concentrated) to give the Present compound (Ia).

V is preferably a fluorine atom.

Process 4

The Present compound (I) may be prepared by reacting a compoundrepresented by formula (M-4) (hereinafter referred to as “Compound(M-4)”) with a compound represented by formula (R-15) (hereinafterreferred to as “Compound (R-15)”) in the presence of a base.

[wherein the symbols are the same as defined above.]

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include ethers, aromatichydrocarbons, nitriles, aprotic polar solvents, and mixed solventsthereof.

Examples of the base to be used in the reaction include alkali metalcarbonates and alkali metal hydrides.

In the reaction, the Compound (R-4) is usually used within a range of 1to 10 molar ratio(s), and the base is usually used within a range of 1to 10 molar ratio(s), relative to 1 mole of the Compound (M-4).

The reaction temperature of the reaction is usually within a range of−20° C. to 150° C. The reaction period of the reaction is usually withina range of 0.5 to 24 hours.

When the reaction is completed, the reaction mixture is extracted withorganic solvent(s), and the organic layers are worked up (for example,dried or concentrated) to give the Present compound (I).

V is preferably a fluorine atom.

Hereinafter, a process for preparing each Intermediate compound isdescribed.

Reference Process 1

The Compound (M-1) may be prepared by reacting a compound represented byformula (M-8) (hereinafter referred to as “Compound (M-8)”) with acompound represented by formula (M-9) (hereinafter referred to as“Compound (M-9)”) in the presence of a metal catalyst.

[wherein: V³ represents a chlorine atom, a bromine atom, or an iodineatom; M represents a B(OR⁴⁰)₂, a4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl group, a Sn(n-C₄H₉)₃, aZnCl, a MgCl, or a MgBr; R⁴⁰ represents a hydrogen atom or a C1-C6 alkylgroup; and the other symbols are the same as defined above.]

The Compound (M-9) may be prepared according to, for example, theprocess described in WO 03/024961 pamphlet or the process described inOrganic Process Research & Development, 2004, 8, 192-200.

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include ethers, aromatichydrocarbons, aprotic polar solvents, water, and mixed solvents thereof.

Examples of the metal catalyst to be used in the reaction includepalladium catalysts such as tetrakis(triphenylphosphine)palladium(0),1,1′-bis(diphenylphosphino)ferrocene palladium(II) dichloride,tris(dibenzylideneacetone)dipalladium(0), and palladium(II) acetate;nickel catalysts such as bis(cyclooctadiene)nickel(0) and nickel(II)chloride; and copper catalysts such as copper(I) iodide and copper(I)chloride.

A ligand, a base, and/or an inorganic halide may be added to thereaction as needed.

Examples of the ligand to be used in the reaction includetriphenylphosphine, Xantphos,2,2′-bis(diphenylphosphino)-1,1′-binaphthyl,1,1′-bis(diphenylphosphino)ferrocene,2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl,2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl,1,2-bis(diphenylphosphino)ethane, 2,2′-bipyridine, 2-aminoethanol,8-hydroxyquinoline, and 1,10-phenanthroline.

Examples of the base to be used in the reaction include alkali metalhydrides, alkali metal carbonates, and organic bases.

Examples of the inorganic halide to be used in the reaction includealkali metal fluorides such as potassium fluoride and sodium fluoride;and alkali metal chlorides such as lithium chloride and sodium chloride.

In the reaction, the Compound (M-9) is usually used within a range of 1to 10 molar ratio(s), the metal catalyst is usually used within a rangeof 0.01 to 0.5 molar ratios, the ligand is usually used within a rangeof 0.01 to 1 molar ratio(s), the base is usually used within a range of0.1 to 5 molar ratios, and the inorganic halide is usually used within arange of 0.1 to 5 molar ratios, relative to 1 mole of the Compound(M-8).

The reaction temperature of the reaction is usually within a range of−20° C. to 200° C. The reaction period of the reaction is usually withina range of 0.1 to 24 hours.

When the reaction is completed, the reaction mixture is extracted withorganic solvent(s), and the organic layers are worked up (for example,dried or concentrated) to give the Compound (M-1).

Reference Process 2

The Compound (M-3) may be prepared by reacting a compound represented byformula (M-11) (hereinafter referred to as “Compound (M-11)”) with anacid.

[wherein: R^(x) represents a methyl group or an ethyl group; and theother symbols are the same as defined above.]

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include aliphatic halogenatedhydrocarbons, aromatic hydrocarbons, nitriles, alcohols, acetic acid,water, and mixed solvents thereof.

Examples of the acid to be used in the reaction include mineral acidssuch as hydrochloric acid; halogenated borons such as boron trichlorideand boron tribromide; and metal chlorides such as titanium chloride andaluminum chloride.

In the reaction, the acid is usually used within a range of 0.1 to 10molar ratio(s) relative to 1 mole of the Compound (M-11). When a mineralacid is used as the acid, the mineral acid may be used also as asolvent.

The reaction temperature of the reaction is usually within a range of−20° C. to 150° C. The reaction period of the reaction is usually withina range of 0.1 to 24 hours.

When the reaction is completed, the reaction mixture is extracted withorganic solvent(s), and the organic layers are worked up (for example,dried or concentrated) to give the Compound (M-3).

Reference Process 3

In the Compound (M-11), a compound wherein n represents 0 (hereinafterreferred to as “Compound (M-11a)”), a compound wherein n represents 1(hereinafter referred to as “Compound (M-11b)”), and a compound whereinn represents 2 (hereinafter referred to as “Compound (M-11c)”) may beprepared according to the following process.

[wherein the symbols are the same as defined above.]

The Compound (M-13) may be prepared by using a compound represented byformula (M-12) (hereinafter referred to as “Compound (M-12)”) instead ofthe Compound (M-8) according to the process described in the Referenceprocess 1.

The Compound (M-12) is a commercially available compound or may beprepared according to a known process.

The Compound (M-11a) may be prepared by using the Compound (M-13)instead of the Compound (M-1) according to the process described in theProcess 3.

The Compound (M-11b) and the Compound (M-11c) may be prepared by usingthe Compound (M-1a) instead of the Present compound (Ia) according tothe process described in the Process 1.

Reference Process 4

A compound represented by formula (M-4a) (hereinafter referred to as“Compound (M-4a)”) and a compound represented by formula (M-4b)(hereinafter referred to as “Compound (M-4b)”) may be prepared accordingto the following process.

[wherein: V⁴ represents a chlorine atom or a bromine atom; V⁵ representsa fluorine atom or an iodine atom; and the other symbols are the same asdefined above.]

First, a process for preparing the Compound (M-4a) from the Compound(M-3) is described.

The Compound (M-4a) may be prepared by reacting the Compound (M-3) withphosphorus oxychloride or phosphorus oxybromide.

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include aromatic hydrocarbons.

When phosphorus oxychloride is used, phosphorus oxychloride may be usedalso as a solvent.

In the reaction, phosphorus oxychloride or phosphorus oxybromide isusually used within a range of 1 to 10 molar ratio(s) relative to 1 moleof the Compound (M-3).

The reaction temperature of the reaction is usually within a range of 0°C. to 150° C. The reaction period of the reaction is usually within arange of 0.5 to 24 hours.

When the reaction is completed, the reaction mixture is extracted withorganic solvent(s), and the organic layers are worked up (for example,dried or concentrated) to give the Compound (M-4a).

Next, a process for preparing the Compound (M-4b) from the Compound(M-4a) is described.

The Compound (M-4b) may be prepared by reacting the Compound (M-4a) withan inorganic fluoride or an inorganic iodide.

The reaction is usually carried out in a solvent. Examples of thesolvent to be used in the reaction include nitriles, aprotic polarsolvents, nitrogen-containing aromatic compounds, and mixed solventsthereof.

Examples of the inorganic fluoride to be used in the reaction includepotassium fluoride, sodium fluoride, and cesium fluoride.

Examples of the inorganic iodide to be used in the reaction includepotassium iodide and sodium iodide.

When the Compound (M-4b) wherein V⁵ represents a fluorine atom isprepared, the inorganic fluoride is usually used within a range of 1 to10 molar ratio(s) relative to 1 mole of the Compound (M-4a).

When the Compound (M-4b) wherein V⁵ represents an iodine atom isprepared, the inorganic iodide is usually used within a range of 1 to 10molar ratio(s) relative to 1 mole of the Compound (M-4a).

The reaction temperature of the reaction is usually within a range of 0°C. to 250° C. The reaction period of the reaction is usually within arange of 0.5 to 24 hours.

When the reaction is completed, the reaction mixture is extracted withorganic solvent(s), and the organic layers are worked up (for example,dried or concentrated) to give the Compound (M-4b).

Next, specific examples of the Present compound are shown below.

The Present compound represented by formula (1-A)

wherein n represents 2, R^(3b) represents a trifluoromethyl group,R^(3a), R^(3c), R^(3d), R^(6a), R^(6b), and R^(6c) represent each ahydrogen atom, and R¹ and R² represent any one combination indicated inTable 1 to Table 5 (hereinafter referred to as “Compound group SX1”).

TABLE 1 R¹ R² CF₂HCH₂ CH₃CH₂ CH₃CF₂ CH₃CH₂ CF₃CH₂ CH₃CH₂ CCl₃CH₂ CH₃CH₂CF₂HCF₂ CH₃CH₂ CHClFCF₂ CH₃CH₂ CF₃CH₂CH₂ CH₃CH₂ CF₂HCF₂CH₂ CH₃CH₂CF₃CF₂CH₂ CH₃CH₂ CBrF₂CF₂ CH₃CH₂ CF₃CFHCF₂ CH₃CH₂ CH₃CF₂CH₂ CH₃CH₂CF₃CH(CH₃) CH₃CH₂ CF₃C(CH₃)₂ CH₃CH₂ CH(CH₃)₂CH(CF₃) CH₃CH₂ (CF₃)₂CHCH₃CH₂ CH₃CH₂CH(CF₃) CH₃CH₂ CF₃CCl₂CH₂ CH₃CH₂ CF₃CF₂CH(CH₃) CH₃CH₂CF₃CF₂CH(CH₂CH₃) CH₃CH₂ C(CH₃)(CF₃)₂CH₂ CH₃CH₂ CF₃CFHCF₂CH₂ CH₃CH₂CF₃(CF₂)₂CH₂ CH₃CH₂ CBrF₂CF₂CH₂CH₂ CH₃CH₂ CF₃CFHCF₂CH(CH₃) CH₃CH₂

TABLE 2 R¹ R² CF₃CH═CHCH₂ CH₃CH₂ CF₃(CF₂)₃CH₂ CH₃CH₂ CF₃(CF₂)₄CH₂ CH₃CH₂CF₃(CF₂)₃CH₂CH₂ CH₃CH₂ CF(CF₃)₂CF₂CF₂CH₂CH₂ CH₃CH₂ CF₂H(CF₂)₃CH₂ CH₃CH₂CF₂H(CF₂)₅CH₂ CH₃CH₂ CF₃(CF₂)₃CH₂CH₂CH₂ CH₃CH₂ CF₃CF₂(CH₂)₅CH₂ CH₃CH₂CF₃(CF₂)₅CH₂CH₂CH₂ CH₃CH₂ CF₃(CF₂)₃CH₂(CH₂)₄CH₂ CH₃CH₂ CF₃(CF₂)₅CH₂CH₂CH₃CH₂ CF(CF₃)₂CH₂(CH₂)₄CH₂ CH₃CH₂ CF₃OCFHCF₂ CH₃CH₂ CH₃OCH₂CF₂CH₂CH₃CH₂ CF₃CH₂OCH₂CF₂CH₂ CH₃CH₂ CH₂FCF₂CH₂ CH₃CH₂ CH₂ClCF₂CH₂ CH₃CH₂CH₂BrCF₂CH₂ CH₃CH₂ CH₃OCH₂(CF₂)₂CH₂ CH₃CH₂ CF₃CH₂OCH₂(CF₂)₂CH₂ CH₃CH₂CH₂F(CF₂)₂CH₂ CH₃CH₂ CH₂Cl(CF₂)₂CH₂ CH₃CH₂ CH₂Br(CF₂)₂CH₂ CH₃CH₂CH₃OCH₂(CF₂)₃CH₂ CH₃CH₂

TABLE 3 R¹ R² CF₃CH₂OCH₂(CF₂)₃CH₂ CH₃CH₂ CH₃OCH₂(CF₂)₃CH₂ CH₃CH₂CF₃CH₂OCH₂(CF₂)₃CH₂ CH₃CH₂ CH₂F(CF₂)₃CH₂ CH₃CH₂ CH₂Cl(CF₂)₃CH₂ CH₃CH₂CH₂Br(CF₂)₃CH₂ CH₃CH₂ CH₃OCH₂(CF₂)₄CH₂ CH₃CH₂ CF₃CH₂OCH₂(CF₂)₄CH₂ CH₃CH₂CH₂F(CF₂)₄CH₂ CH₃CH₂ CH₂Cl(CF₂)₄CH₂ CH₃CH₂ CH₂Br(CF₂)₄CH₂ CH₃CH₂CF₃CF₂OCFHCF₂ CH₃CH₂ CF₃CF₂CF₂OCFHCF₂ CH₃CH₂ CF₃CF₂CF₂OCF(CF₃)CH₂ CH₃CH₂CF₃CH₂OCH₂CH₂ CH₃CH₂

TABLE 4 R¹ R²

CH₃CH₂

CH₃CH₂

CH₃CH₂

CH₃CH₂

CH₃CH₂

CH₃CH₂

CH₃CH₂

TABLE 5 R¹ R² CH₃SCH₂CF₂CH₂ CH₃CH₂ CH₃S(O)CH₂CF₂CH₂ CH₃CH₂CH₃S(O)₂CH₂CF₂CH₂ CH₃CH₂ CF₃CH₂SCH₂CF₂CH₂ CH₃CH₂ CF₃CH₂S(O)CH₂CF₂CH₂CH₃CH₂ CF₃CH₂S(O)₂CH₂CF₂CH₂ CH₃CH₂ CF₃SCH₂CF₂CH₂ CH₃CH₂ CF₃S(O)CH₂CF₂CH₂CH₃CH₂ CF₃S(O)₂CH₂CF₂CH₂ CH₃CH₂ CF₃SCH₂(CF₂)₂CH₂ CH₃CH₂CF₃S(O)CH₂(CF₂)₂CH₂ CH₃CH₂ CF₃S(O)₂CH₂(CF₂)₂CH₂ CH₃CH₂ CF₃SCH₂(CF₂)₃CH₂CH₃CH₂ CF₃S(O)CH₂(CF₂)₃CH₂ CH₃CH₂ CF₃S(O)₂CH₂(CF₂)₃CH₂ CH₃CH₂CF₃SCH₂(CF₂)₄CH₂ CH₃CH₂ CF₃S(O)CH₂(CF₂)₄CH₂ CH₃CH₂ CF₃S(O)₂CH₂(CF₂)₄CH₂CH₃CH₂ CF₃CH₂SCH₂CH₂ CH₃CH₂ CF₃CH₂S(O)CH₂CH₂ CH₃CH₂ CF₃CH₂S(O)₂CH₂CH₂CH₃CH₂ CF₃SCH₂CH₂ CH₃CH₂ CF₃S(O)CH₂CH₂ CH₃CH₂ CF₃S(O)₂CH₂CH₂ CH₃CH₂

The Present compound represented by formula (I-A), wherein n represents2, R^(3a), R^(3b), R^(3c), R^(3d), R^(6a), R^(6b), and R^(6c) representeach a hydrogen atom, and R¹ and R² represent any one combinationindicated in Table 1 to Table 5 (hereinafter referred to as “Compoundgroup SX2”).

The Present compound represented by formula (I-A), wherein n represents2, R^(3b) represents a chlorine atom, R^(3a)R^(3c), R^(3d), R^(6a),R^(6b) and R^(6c) represent each a hydrogen atom, and R¹ and R²represent any one combination indicated in Table 1 to Table 5(hereinafter referred to as “Compound group SX3”).

The Present compound represented by formula (I-A), wherein n represents2, R^(3b) represents a fluorine atom, R^(3a), R^(3c), R^(3d), R^(6a),R^(6b), and R^(6c) represent each a hydrogen atom, and R¹⁰¹ and R¹⁰²represent any one combination indicated in Table 1 to Table 5(hereinafter referred to as “Compound group SX4”).

The Present compound represented by formula (I-A), wherein n represents2, R^(3b) represents a bromine atom, R^(3a), R^(3c), R^(3d), R^(6a),R^(6b), and R^(6c) represent each a hydrogen atom, and R¹⁰¹ and R¹⁰²represent any one combination indicated in Table 1 to Table 5(hereinafter referred to as “Compound group SX5”).

The Present compound represented by formula (I-A), wherein n represents2, R^(3b) represents a trifluoromethoxy group, R^(3a), R^(3c), R^(3d),R^(6a), R^(6b), and R^(6c) represent each a hydrogen atom, and R¹ and R²represent any one combination indicated in Table 1 to Table 5(hereinafter referred to as “Compound group SX6”).

The Present compound represented by formula (I-A), wherein n represents2, R^(3b) represents a trifluoromethylthio group, R^(3a), R^(3c),R^(3d), R^(6a), R^(6b), and R^(6c) represent each a hydrogen atom, andR¹ and R² represent any one combination indicated in Table 1 to Table 5(hereinafter referred to as “Compound group SX7”).

The Present compound represented by formula (I-A), wherein n represents2, R^(3b) represents a trifluoromethylsulfinyl group, R^(3a), R^(3c),R^(3d), R^(6a), R^(6b), and R^(6c) represent each a hydrogen atom, andR¹ and R² represent any one combination indicated in Table 1 to Table 5(hereinafter referred to as “Compound group SX8”).

The Present compound represented by formula (I-A), wherein n represents2, R^(3b) represents a trifluoromethylsulfonyl group, R^(3a),R^(3c)R^(3d), R^(6a), R^(6b), and R^(6c) represent each a hydrogen atom,and R¹ and R² represent any one combination indicated in Table 1 toTable 5 (hereinafter referred to as “Compound group SX9”).

The Present compound represented by formula (I-A), wherein n represents2, R^(3b) represents a pentafluoroethyl group, R^(3a), R^(3c), R^(3d),R^(6a), R^(6b), and R^(6c) represent each a hydrogen atom, and R and R²represent any one combination indicated in Table 1 to Table 5(hereinafter referred to as “Compound group SX10”).

The Present compound represented by formula (I-A), wherein n represents2, R^(3b) represents a pentafluorosulfanyl group, R^(3a), R^(3c)R^(3d),R^(6a), R^(6b), and R^(6c) represent each a hydrogen atom, and R¹ and R²represent any one combination indicated in Table 1 to Table 5(hereinafter referred to as “Compound group SX11”).

The Present compound represented by formula (I-A), wherein n represents2, R^(3b) represents a pyridin-2-yl group, R^(3a), R^(3c), R^(3d),R^(6a), R^(6b), and R^(6c) represent each a hydrogen atom, and R¹ and R²represent any one combination indicated in Table 1 to Table 5(hereinafter referred to as “Compound group SX12”).

The Present compound represented by formula (I-A), wherein n represents2, R^(3b) represents a pyridin-3-yl group, R^(3a), R^(3c), R^(3d),R^(6a), R^(6b), and R^(6c) represent each a hydrogen atom, and R¹ and R²represent any one combination indicated in Table 1 to Table 5(hereinafter referred to as “Compound group SX13”).

The Present compound represented by formula (I-A), wherein n represents2, R^(3b) represents a pyridin-4-yl group, R^(3a), R^(3c), R^(3d),R^(6a), R^(6b), and R^(6c) represent each a hydrogen atom, and R¹ and R²represent any one combination indicated in Table 1 to Table 5(hereinafter referred to as “Compound group SX14”).

The Present compound represented by formula (I-A), wherein n represents2, R^(3b) represents a pyridazin-3-yl group, R^(3a), R^(3c), R^(3d),R^(6a), R^(6b), and R^(6c) represent each a hydrogen atom, and R¹ and R²represent any one combination indicated in Table 1 to Table 5(hereinafter referred to as “Compound group SX15”).

The Present compound represented by formula (I-A), wherein n represents2, R^(3b) represents a pyridazin-4-yl group, R^(3a), R^(3c), R^(3d),R^(6a), R^(6b), and R^(6c) represent each a hydrogen atom, and R¹ and R²represent any one combination indicated in Table 1 to Table 5(hereinafter referred to as “Compound group SX16”).

The Present compound represented by formula (I-A), wherein n represents2, R^(3b) represents a pyrimidin-2-yl group, R^(3a), R^(3c), R^(3d),R^(6a), R^(6b), and R^(6c) represent each a hydrogen atom, and R¹ and R²represent any one combination indicated in Table 1 to Table 5(hereinafter referred to as “Compound group SX17”).

The Present compound represented by formula (I-A), wherein n represents2, R^(3b) represents a pyrimidin-4-yl group, R^(3a), R^(3c)R^(3d),R^(6a), R^(6b), and R^(6c) represent each a hydrogen atom, and R¹ and R²represent any one combination indicated in Table 1 to Table 5(hereinafter referred to as “Compound group SX18”).

The Present compound represented by formula (I-A), wherein n represents2, R^(3b) represents a pyrimidin-5-yl group, R^(3a), R^(3c), R^(3d),R^(6a), R^(6b), and R^(6c) represent each a hydrogen atom, and R¹ and R²represent any one combination indicated in Table 1 to Table 5(hereinafter referred to as “Compound group SX19”).

The Present compound represented by formula (I-A), wherein n represents2, R^(3b) represents a pyrazin-5-yl group, R^(3a), R^(3c), R^(3d),R^(6a), R^(6b), and R^(6c) represent each a hydrogen atom, and R¹ and R²represent any one combination indicated in Table 1 to Table 5(hereinafter referred to as “Compound group SX20”).

The Present compound may be mixed with or used in combination with aknown pesticide, miticide, nematicide, fungicide, plant growthregulator, or synergist such as the followings. Hereinafter, examples ofcombinations of active ingredients which may be mixed with or used incombination with are described. The abbreviation of “SX” indicates “anyone of the Present compound selected from the Compound groups SX1 toSX20”. Also, the number in parentheses represents the CAS registrationnumber.

clothianidin (205510-53-8)+SX, thiamethoxam (153719-23-4)+SX,imidacloprid (138261-41-3)+SX, thiacloprid (111988-49-9)+SX,flupyradifurone (951659-40-8)+SX, sulfoxaflor (946578-00-3)+SX,triflumezopyrim (1263133-33-0)+SX, dicloromezotiaz (1263629-39-5)+SX,beta-cyfluthrin (68359-37-5)+SX, tefluthrin (79538-32-2)+SX, fipronil(120068-37-3)+SX, chlorantraniliprole (500008-45-7)+SX, cyantraniliprole(736994-63-1)+SX, tetraniliprole (1229654-66-3)+SX, thiodicarb(59669-26-0)+SX, carbofuran (1563-66-2)+SX, fluxametamide(928783-29-3)+SX, afoxolaner (1093861-60-9)+SX, fluralaner(864731-61-3)+SX, broflanilide (1207727-04-5)+SX, tebuconazole(107534-96-3)+SX, prothioconazole (178928-70-6)+SX, metconazole(125116-23-6)+SX, ipconazole (125225-28-7)+SX, triticonazole(131983-72-7)+SX, difenoconazole (119446-68-3)+SX, imazalil(35554-44-0)+SX, triadimenol (55219-65-3)+SX, tetraconazole(112281-77-3)+SX, flutriafol (76674-21-0)+SX, mandestrobin(173662-97-0)+SX, azoxystrobin (131860-33-8)+SX, pyraclostrobin(175013-18-0)+SX, trifloxystrobin (141517-21-7)+SX, fluoxastrobin(193740-76-0)+SX, picoxystrobin (117428-22-5)+SX, fenamidone(161326-34-7)+SX, metalaxyl (57837-19-1)+SX, metalaxyl-M(70630-17-0)+SX, fludioxonil (131341-86-1)+SX, sedaxane(874967-67-6)+SX, penflufen (494793-67-8)+SX, fluxapyroxad(907204-31-3)+SX, fluopyram (658066-35-4)+SX, benzovindiflupyr(1072957-71-1)+SX, boscalid (188425-85-6)+SX, carboxin (5234-68-4)+SX,penthiopyrad (183675-82-3)+SX, flutolanil (66332-96-5)+SX, captan(133-06-2)+SX, thiram (137-26-8)+SX, tolclofos-methyl (57018-04-9)+SX,thiabendazole (148-79-8)+SX, ethaboxam (162650-77-3)+SX, mancozeb(8018-01-7)+SX, picarbutrazox (500207-04-5)+SX, oxathiapiprolin(1003318-67-9)+SX, silthiofam (175217-20-6)+SX, abamectin(71751-41-2)+SX, fluensulfone (318290-98-1)+SX, fluazaindolizine(1254304-22-7)+SX, tioxazafen (330459-31-9)+SX,3-difluoromethyl-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide(141573-94-6)+SX, 3-difluoromethyl-1-methyl-N-[(3R)-,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide (1352994-67-2)+SX, thecompound represented by the following formula:

(1689566-03-7)+SX, Mycorrhiza Fungi+SX, Bacillus firmus+SX, Bacillusamyloliquefaciens+SX, Pasteuria nishizawae+SX, and Pasteuriapenetrans+SX.

Examples of the harmful arthropod on which the Present compound hasefficacies include harmful insects and harmful mites. Specific examplesof the harmful arthropod include the followings.

Hemiptera Pests:

Delphacidae (for example, Laodelphax striatellus, Nilaparvata lugens,Sogatella furcifera, or Peregrinus maidis);

Cicadellidae (for example, Nephotettix cincticeps, Nephotettixvirescens, Nephotettix nigropictus (Rice green leafhopper), Reciliadorsalis, Empoasca onukii, Empoasca fabae, Dalbulus maidis, Mahanarvaposticata (Sugarcane froghopper), Mahanarva fimbriolota (Sugarcane rootspittlebug), Cofana spectra, Nephotettix nigropictus, or Reciliadorsalis);

Aphididae (for example, Aphis gossypii, Myzus persicae, Brevicorynebrassicae, Aphis spiraecola, Macrosiphum euphorbiae, Aulacorthum solani,Rhopalosiphum padi, Toxoptera citricidus, Hyalopterus pruni, Aphisglycines Matsumura, Rhopalosiphum maidis, Tetraneura nigriabdominalis,Viteus vitifoliae, Daktulosphaira vitifoliae (Grape Phylloxera),Phylloxera devastatrix Pergande (Pecan phylloxera), Phylloxera notabilispergande (Pecan leaf phylloxera), or Phylloxera russellae Stoetzel(Southern pecan leaf phylloxera));

Pentatomidae (for example, Scotinophara lurida, Scotinophara coarctata(Malayan rice black bug), Nezara antennata, Eysarcoris parvus,Halyomorpha mista, Nezara viridula, Euschistus heros (Brown stink bug),Nezara viridula (Southern green stink bug), Piezodorus guildinii (Redbanded stink bug), Scaptocoris castanea (Burrower brown bug), Oebaluspugnax, or Dichelops melacanthus);

Alydidae (for example, Riptortus clavetus, Leptocorisa chinensis,Leptocorisa acuta, or Leptocorisa spp.);

Miridae (for example, Trigonotylus caelestialium, Stenotusrubrovittatus, Lygus lineolaris, or Blissus leucopterus leucopterus(Chinchi bug));

Aleyrodidae (for example, Trialeurodes vaporariorum, Bemisia tabaci,Dialeurodes citri, or Aleurocanthus spiniferus);

Coccoidea (for example, Aonidiella aurantii, Comstockaspis perniciosa,Unaspis citri, Ceroplastes rubens, Icerya purchasi, Planococcuskraunhiae, Pseudococcus longispinis, Pseudaulacaspis pentagona, orBrevennia rehi);

Psyllidae (for example, Diaphorina citri, Psylla pyrisuga, orBactericerca cockerelli);

Tingidae (for example, Stephanitis nasi);

Cimicidae (for example, Cimex lectularius);

Quesada gigas (Giant Cicada);

and the others.

Lepidoptera Pests:

Pyralidae (for example, Chilo suppressalis, Chilo polychrysus(Darkheaded stm borer), Tryporyza incertulas, Chilo polychrysus,Scirpophaga innotata, Scirpophaga incertulas (Yellow stem borer),Sesamia inferens (Pink borer), Rupela albinella, Cnaphalocrocismedinalis, Marasmia patnalis, Marasmia exigna, Notarcha derogata, Plodiainterpunctella, Ostrinia furnacalis, Hellula undalis, Pediasiateterrellus, Nymphula depunctalis, Marasmia spp., Hydraecia immanis (Hopvine borer), Ostrinia nubilalis (European corn borer), Elasmopalpuslignosellus (Lesser cornstalk borer), Epinotia aporema (Bean ShootBorer), Diatraea saccharalis (Sugarcane borer), or Telchin licus (GiantSugarcane borer));

Noctuidae (for example, Spodoptera litura, Spodoptera exigua,Pseudaletia separata, Mamestra brassicae, Sesamia inferens, Spodopteramauritia, Spodoptera frugiperda, Spodoptera exempta, Agrotis ipsilon,Plusia nigrisigna, Pseudoplusia includens (Soybean looper), Trichoplusiaspp., Heliothis spp. (for example, Heliothis virescens), Helicoverpaspp. (for example, Helicoverpa armigera), Anticarsia gammatalis(Velvetbean caterpillar), or Alabama argillacea (Cotton leafworm));

Pieridae (for example, Pieris rapae);

Tortricidae (for example, Adoxophyes spp., Grapholita molesta,Leguminivora glycinivorella, Matsumuraeses azukivora, Adoxophyes oranafasciata, Adoxophyes honmai, Homona magnanima, Archips fuscocupreanus,or Cydia pomonella);

Gracillariidae (for example, Caloptilia theivora or Phyllonorycterringoneella);

Carposinidae (for example, Carposina niponensis or Ecdytolophaaurantiana (Citrus fruit borer));

Lyonetiidae (for example, Leucoptera coffeela (Coffee Leaf miner) orLyonetia spp.);

Lymantriidae (for example, Lymantria spp. or Euproctis spp.);

Yponomeutidae (for example, Plutella xylostella);

Gelechiidae (for example, Pectinophora gossypiella or Phthorimaeaoperculella);

Arctiidae (for example, Hyphantria cunea);

and the others.

Thysanoptera Pests:

Thripidae (for example, Frankliniella occidentalis, Thrips parmi,Scirtothrips dorsalis, Thrips tabaci, Frankliniella intonsa,Frankliniella occidentalis, Haplothrips aculeatus, or Stenchaetothripsbiformis);

and the others.

Diptera Pests:

House mosquitoes (Culex spp.) (for example, Culex pipiens pallens, Culextritaeniorhynchus, or Culex quinquefasciatus);

Aedes spp. (for example, Aedes aegypti or Aedes albopictus);

Anopheles spp. (for example, Anopheles sinensis);

Chironomidae;

Muscidae (for example, Musca domestica or Muscina stabulans);

Anthomyiidae (for example, Delia platura, Delia antiqua, or Tetanopsmyopaeformis);

Agromyzidae (for example, Agromyza oryzae, Hydrellia griseola, Liriomyzasativae, Liriomyza trifolii, or Chromatomyia horticola);

Chloropidae (for example, Chlorops oryzae);

Tephritidae (for example, Dacus cucurbitae or Ceratitis capitata);

Ephydridae (for example, Hydrellia philippina or Hydrellia sasakii);

Drosophilidae;

Phoridae (for example, Megaselia spiracularis);

Psychodidae (for example, Clogmia albipunctata);

Sciaridae;

Cecidomyiidae (for example, Mayetiola destructor or Orseolia oryzae);

Diopsidae (for example, Diopsis macrophthalma);

Tipulidae (for example, Tipula oleracea (Common cranefly) or Tipulapaludosa (European cranefly));

and the others.

Coleoptera Pests:

Chrysomelidae (for example, Diabrotica virgifera virgifera, Diabroticaundecimpunctata howardi, Diabrotica barberi, Diabrotica virgifera zeae,Diabrotica balteata LeConte, Diabrotica speciosa, Diabrotica speciosa(Cucurbit Beetle), Cerotoma trifurcata, Oulema melanopus, Aulacophorafemoralis, Phyllotreta striolata, Leptinotarsa decemlineata, Oulemaoryzae, Colaspis brunnea, Chaetocnema pulicaria, Epitrix cucumeris,Dicladispa armigera, Stenolophus lecontei (Seedcorn beetle), or Cliviniaimpressifrons (Slender seedcorn beetle));

Scarabaeidae (for example, Anomala cuprea, Anomala rufocuprea, Popilliajaponica, Rhizotrogus majalis (European Chafer), Bothynus gibbosus(carrot beetle), Colaspis brunnea (Grape Colaspis), yochrous denticollis(southern Corn leaf beetle), Holotrichia spp., or Phyllophaga spp. (forexample, Phyllophaga crinita));

Erirhinidae (for example, Sitophilus zeamais, Echinocnemus squameus,Lissorhoptrus oryzophilus, or Sphenophorus venatus);

Curculionidae (for example, Anthonomus grandis, Sphenophorus callosus(Southern Corn Billbug), Sternechus subsignatus (Soybean stalk weevil),or Sphenophorus spp. (for example, Sphenophorus levis));

Epilachna (for example, Epilachna vigintioctopunctata);

Scolytidae (for example, Lyctus brunneus or Tomicus piniperda);

Bostrychidae;

Ptinidae;

Cerambycidae (for example, Anoplophora malasiaca or Migdolus fryanus);

Elateridae (Agriotes sp., Aelous sp., Anchastus sp., Melanotus sp.,Limonius sp., Conoderus sp., Ctenicera sp.) (for example, Melanotusokinawensis, Agriotes ogurae fuscicollis, or Melanotus legatus);

Staphylinidae (for example, Paederus fuscipes);

Hypothenemus hampei (Coffee Barry Borer);

and the others.

Orthoptera Pests:

Locusta migratoria, Gryllotalpa africana, Dociostaurus maroccanus,Chortoicetes terminifera, Nomadacris septemfasciata, Locustana pardalina(Brown Locust), Anacridium melanorhodon (Tree Locust), Calliptamusitalicus (Italian Locust), Melanoplus differentialis (Differentialgrasshopper), Melanoplus bivittatus (Twostriped grasshopper), Melanoplussanguinipes (Migratory grasshopper), Melanoplus femurrubrum (Red-Leggedgrasshopper), Camnula pellucida (Clearwinged grasshopper), Schistocercagregaria, Gastrimargus musicus (Yellow-winged locust), Austracrisguttulosa (Spur-throated locust), Oxya yezoensis, Oxya japonica, Patangasuccincta, or Gryllidae (for example, Acheta domesticus, Teleogryllusemma, or Anabrus simplex (Mormon cricket));

and the others.

Hymenoptera Pests:

Tenthredinidae (for example, Athalia rosae or Athalia japonica);

Solenopsis spp.;

Attini spp. (for example, Atta capiguara (Brown leaf-cutting ant));

and the others.

Blattodea Pests:

Blattella germanica, Periplaneta fuliginosa, Periplaneta americana,Periplaneta brunnea, Blatta orientalis, and the others.

Termitidae Pests:

Reticulitermes speratus, Coptotermes formosanus, Incisitermes minor,Cryptotermes domesticus, Odontotermes formosanus, Neotermes koshunensis,Glyptotermes satsumensis, Glyptotermes nakajimai, Glyptotermes fuscus,Glyptotermes kodamai, Glyptotermes kushimensis, Hodotermopsis sjostedti,Coptotermes guangzhoensis, Reticulitermes amamianus, Reticulitermesmiyatakei, Reticulitermes kanmonensis, Nasutitermes takasagoensis,Pericapritermes nitobei, Sinocapritermes mushae, Cornitermes cumulans,and the others.

Acarina Pests:

Tetranychidae (for example, Tetranychus urticae, Tetranychus kanzawai,Panonychus citri, Panonychus ulmi, Oligonychus spp., or Brevipalpusphoenicis (Southern Turkey spider mites));

Eriophyidae (for example, Aculops pelekassi, Phyllocoptruta citri,Aculops lycopersici, Calacarus carinatus, Acaphylla theavagrans,Eriophyes chibaensis, or Aculus schlechtendali);

Tarsonemidae (for example, Polyphagotarsonemus latus);

Tenuipalpidae (for example, Brevipalpus phoenicis);

Tuckerellidae;

Ixodidae (for example, Haemaphysalis longicornis, Haemaphysalis flava,Dermacentor taiwanicus, Dermacentor variabilis, Ixodes ovatus, Ixodespersulcatus, Ixodes scapularis, Amblyomma americanum, Boophilusmicroplus, or Rhipicephalus sanguineus);

Acaridae (for example, Tyrophagus putrescentiae or Tyrophagus similis);

Pyroglyphidae (for example, Dermatophagoides farinae or Dermatophagoidesptrenyssnus);

and the others.

The agent for controlling harmful arthropods of the present inventioncomprises the Present compound and an inert carrier. The agent forcontrolling harmful arthropods of the present invention is usuallyprepared by mixing the Present compound with an inert carrier such assolid carriers, liquid carriers, or gaseous carriers, and if necessary,adding surfactants and the other auxiliary agents for formulation, toformulate into emulsifiable concentrates, oil solutions, dustformulations, granules, wettable powders, flowables, microcapsules,aerosols, smoking agents, poison baits, resin formulations, shampooformulations, paste-like formulations, foams, carbon dioxideformulations, tablets, or the others. Such formulations may be processedinto and used as mosquito repellent coils, electric mosquito repellentmats, liquid mosquito formulations, smoking agents, fumigants, sheetformulations, spot-on formulations, or formulations for oral treatment.Also, the agent for controlling harmful arthropods of the presentinvention may be mixed with other pesticides, miticides, nematicides,fungicides, plant growth regulators, herbicides, or synergists.

The agent for controlling harmful arthropods of the present inventionusually comprises 0.01 to 95% by weight of the Present compound.

Examples of the solid carriers to be used in the formulation includefine powders or granules of clays (for example, kaolin clay,diatomaceous earth, bentonite, Fubasami clay, or acid white clay),synthetic hydrated silicon oxides, talcs, ceramics, other inorganicminerals (for example, sericite, quartz, sulfur, active carbon, calciumcarbonate, or hydrated silica), chemical fertilizers (for example,ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, orammonium chloride), and the others; as well as synthetic resins (forexample, polyester resins such as polypropylene, polyacrylonitrile,polymethylmethacrylate, and polyethylene terephthalate; nylon resinssuch as nylon-6, nylon-11, and nylon-66; polyamide resins; polyvinylchloride, polyvinylidene chloride, vinyl chloride-propylene copolymers,or the others).

Examples of the above-mentioned liquid carriers include water; alcohols(for example, methanol, ethanol, isopropyl alcohol, butanol, hexanol,benzyl alcohol, ethylene glycol, propylene glycol, or phenoxy ethanol);ketones (for example, acetone, methyl ethyl ketone, or cyclohexanone);aromatic hydrocarbons (for example, toluene, xylene, ethyl benzene,dodecyl benzene, phenyl xylyl ethane, or methylnaphthalene); aliphatichydrocarbons (for example, hexane, cyclohexane, kerosene, or light oil);esters (for example, ethyl acetate, butyl acetate, isopropyl myristate,ethyl oleate, diisopropyl adipate, diisobutyl adipate, or propyleneglycol monomethyl ether acetate); nitriles (for example, acetonitrile orisobutyronitrile); ethers (for example, diisopropyl ether, 1,4-dioxane,ethylene glycol dimethyl ether, diethylene glycol dimethyl ether,diethylene glycol monomethyl ether, propylene glycol monomethyl ether,dipropylene glycol monomethyl ether, or 3-methoxy-3-methyl-1-butanol);acid amides (for example, DMF or dimethylacetamide); halogenatedhydrocarbons (for example, dichloromethane, trichloroethane, or carbontetrachloride); sulfoxides (for example, DMSO); propylene carbonate; andvegetable oils (for example, soybean oil or cottonseed oil).

Examples of the above-mentioned gaseous carriers include fluorocarbon,butane gas, liquefied petroleum gas (LPG), dimethyl ether, and carbondioxide gas.

Examples of the surfactants include nonionic surfactants such aspolyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, andpolyethylene glycol fatty acid esters; and anionic surfactants such asalkyl sulfonates, alkylbenzene sulfonates, and alkyl sulfates.

Examples of the other auxiliary agents for formulation include binders,dispersants, colorants, and stabilizers. Specific examples thereofinclude casein, gelatin, saccharides (for example, starch, gum arabic,cellulose derivatives, or alginic acid), lignin derivatives, bentonite,water-soluble synthetic polymers (for example, polyvinyl alcohol,polyvinyl pyrrolidone, or polyacrylic acids), PAP (acidic isopropylphosphate), BHT (2,6-di-tert-butyl-4-methylphenol), and BHA (a mixtureof 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).

Examples of base material of the resin formulation include vinylchloride polymers, polyurethane, and the others, and a plasticizer suchas phthalic acid esters (for example, dimethyl phthalate or dioctylphthalate), adipic acid esters, and stearic acid may be added to thesebase materials, if necessary. The resin formulation may be prepared bymixing the Present compound with the above-mentioned base material,kneading the mixture in a conventional kneading apparatus, followed bymolding it by injection molding, extrusion molding, pressure molding, orthe like. The resultant resin formulation may be subjected to furthermolding, cutting procedure, or the like, if necessary, to be processedinto shapes such as a plate, film, tape, net, and string shape. Theseresin formulations may be processed into animal collars, animal eartags, sheet products, trap strings, gardening supports, or otherproducts.

Examples of the base material for the poison baits include baitingredients such as grain powder, vegetable oil, saccharide, andcrystalline cellulose, and if necessary, with addition of antioxidantssuch as dibutylhydroxytoluene and nordihydroguaiaretic acid,preservatives such as dehydroacetic acid, accidental ingestioninhibitors for children and pets such as a chili powder, insectattraction fragrances such as cheese flavor, onion flavor, and peanutoil, or the other ingredient.

The method for controlling harmful arthropods of the present inventionis conducted by applying an effective amount of the Present compound toa harmful arthropod directly and/or a habitat of pests (for example,plant bodies, soil, an interior of a house, or animal bodies). In themethod for controlling harmful arthropods of the present invention, thePresent compound is usually used in the form of an agent for controllingharmful arthropods of the present invention.

When an agent for controlling harmful arthropods of the presentinvention is used for controlling pests in an agricultural field, theapplication dose as an amount of the Present compound is usually withina range from 1 to 10,000 g per 10,000 m². The emulsifiable concentrate,the wettable powder, or the flowable formulation etc. of an agent forcontrolling harmful arthropods of the present invention is usuallyapplied by diluting it with water in such a way that a concentration ofthe active ingredient is within a range from 0.01 to 10,000 ppm. Thegranular formulation or the dust formulation etc., is usually applied asitself without diluting it.

These formulations and diluents of the formulations with water may bedirectly sprayed to a harmful arthropod or a plant such as a crop to beprotected from a harmful arthropod, or applied to a soil in a cultivatedarea to control a pest that inhabits the soil.

Also, a resin formulation processed into sheet shape or string shape maybe wrapped around a crop, stretched near a crop, spread on a plant footsoil, or the like.

When the agent for controlling harmful arthropods of the presentinvention is used to control pests that live inside a house, theapplication dose as an amount of the Present compound is usually withina range from 0.01 to 1,000 mg per 1 m² of an area to be treated, in thecase of using it on a planar area. In the case of using it spatially,the application dose as an amount of the Present compound is usuallywithin a range from 0.01 to 500 mg per 1 m³ of the space to be treated.When the agent for controlling harmful arthropods of the presentinvention is formulated into emulsifiable concentrates, wettablepowders, flowables, or the others, such formulations are usually appliedafter diluting it with water in such a way that a concentration of theactive ingredient is within a range from 0.1 to 10,000 ppm, and thensparging it. In the case of being formulated into oil solutions,aerosols, smoking agents, poison baits, or the others, such formulationsare used as itself without diluting it.

When the agent for controlling harmful arthropods of the presentinvention is used for controlling external parasites of livestock suchas cows, horses, pigs, sheep, goats, and chickens, and small animalssuch as dogs, cats, rats, and mice, the agent of the present inventionmay be applied to the animals by a known method in the veterinary field.Specifically, when systemic control is intended, the agent of thepresent invention is administered to the animals as a tablet, a mixturewith feed, or a suppository, or by injection (including intramuscular,subcutaneous, intravenous, and intraperitoneal injections), or the like.On the other hand, when non-systemic control is intended, the agent ofthe present invention is applied to the animals by means of spraying ofthe oil solution or aqueous solution, pour-on or spot-on treatment, orwashing of the animal with a shampoo formulation, or by putting a collaror ear tag made of the resin formulations to the animal, or the like. Inthe case of administering to an animal body, the dose of the Presentcompound is usually within a range from 0.1 to 1,000 mg per 1 kg of ananimal body weight.

EXAMPLES

The following Examples including Preparation examples, Formulationexamples, and Test examples serve to illustrate the present inventionmore in detail, which should not intend to limit the present invention.

First, regarding the preparation of the Present compound, thePreparation Examples are shown below.

Preparation Example 1

To a mixture of 2-bromo-5-(2,2,3,3,3-pentafluoropropoxy)pyridine(hereinafter referred to as “Intermediate compound 1”) (2.1 g),2-[2-(ethylsulfanyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolan(hereinafter referred to as “Intermediate compound 2”) (1.0 g), a 2 Msodium carbonate aqueous solution (4.7 mL), and 1,2-dimethoxyethane (11mL) was added tetrakistriphenylphosphinepalladium(0) (220 mg) undernitrogen atmosphere at room temperature. The resulting mixture wasstirred at 80° C. for 3 hours. The resulting reaction mixture wasallowed to stand to room temperature, and then to the mixture was addedwater, and the mixture was extracted with ethyl acetate. The resultingorganic layers were washed with saturated brine and dried over anhydroussodium sulfate, and the organic layers were concentrated under reducedpressure. The resulting residues were subjected to silica gelchromatography to give the Present compound 1 represented by thefollowing formula (1.0 g).

The compounds prepared according to the process described in thePreparation Example 1 and the physical properties thereof are shownbelow.

The compounds represented by formula (I-1)

[wherein the number on the benzene ring represents the binding positionof each substituent.]wherein R¹, (R³)_(q), and n represent any one combination indicated inTable 6.

TABLE 6 Present compound R¹ (R³)_(q) n 1 CF₃CF₂CH₂ H 0 4 CF₂HCF₂CH₂ H 0

Present Compound 1

¹H-NMR (CDCl₃) δ: 8.45 (1H, d), 7.57 (1H, dd), 7.42 (2H, td), 7.37-7.32(2H, m), 7.28-7.23 (1H, m), 4.53 (2H, td), 2.85 (2H, q), 1.24 (3H, t).

Present Compound 4

1H-NMR (CDCl₃) δ: 8.45 (1H, dd), 7.57 (1H, dd), 7.45-7.40 (2H, m),7.37-7.31 (2H, m), 7.28-7.24 (1H, m), 6.25-5.95 (1H, m), 4.47 (2H, tt),2.85 (2H, q), 1.24 (3H, t).

Preparation Example 2

To a suspension of sodium hydride (60%, oily) (1.2 g) and DMSO (24 mL)was added dropwise ethanethiol (2.1 mL) under ice-cooling. The resultingmixture was stirred under ice-cooling for 10 minutes, and then to thereaction mixture was added dropwise a mixed solution of1-bromo-4-chloro-2-fluorobenzene (5.0 g) and DMSO (10 mL). The resultingreaction mixture was stirred at 100° C. for 2 hours. The resultingreaction mixture was allowed to stand to room temperature, and then tothe mixture was added water, and the mixture was extracted with MTBE.The resulting organic layers were dried over anhydrous sodium sulfate,and the organic layers were concentrated under reduced pressure. Theresulting residues were subjected to silica gel chromatography to givethe Intermediate compound 5 represented by the following formula (5.47g).

The compounds prepared according to the process described in thePreparation Example 2 and the physical properties thereof are shownbelow.

The compounds represented by formula (B-1)

[wherein the number on the benzene ring represents the binding positionof each substituent.]wherein R⁴¹ and (R³)_(q) represent any one combination indicated inTable 7, provided that Bn represents a benzyl group.

TABLE 7 Intermediate compound R⁴¹ (R³)_(q) 5 Br 4-Cl 6 Br 5-Cl 7 Br 3-Cl12

4-CF₃

Intermediate Compound 5

¹H-NMR (CDCl₃) δ: 7.44 (1H, d), 7.14 (1H, d), 6.98 (1H, dd), 2.97 (2H,q), 1.40 (3H, t).

Intermediate Compound 6

¹H-NMR (CDCl₃) δ: 7.56 (1H, d), 7.25 (1H, dd), 7.15 (1H, d), 2.95 (2H,q), 1.37 (3H, t).

Intermediate Compound 7

¹H-NMR (CDCl₃) δ: 7.58 (1H, dd), 7.43 (1H, dd), 7.09 (1H, t), 2.96 (2H,q), 1.24 (3H, t).

Intermediate Compound 12

¹H-NMR (CDCl₃) δ: 8.50 (1H, dd), 7.59-7.33 (10H, m), 5.17 (2H, s), 2.90(2H, q), 1.28 (3H, t).

The compounds prepared according to the process described in thePreparation Example 2 and the physical properties thereof are shownbelow.

The compounds represented by formula (I-2)

[wherein the number on the benzene ring represents the binding positionof each substituent.]wherein R¹ and (R³)_(q) represent any one combination indicated in Table8.

TABLE 8 Present compound R¹ (R³)_(q) 15 CF₃CF₂CH₂ 4-OCH₃ 25 CF₃CF₂CH₂3-CF₃ 71 CF₃CF₂CH₂ 4-CF₃ 72 CF₃CF₂CH₂ 6-Cl 73 CF₃CF₂CH₂ 6-CF₃ 31CF₃CF₂CH₂ 4-NO₂ 47 CF₃CF₂CH₂ 4-OCF₃ 74 CF₃CF₂CH₂ 3-Me 56 CF₃CF₂CH₂ 4-Br75 CF₃CF₂CH₂ 5-OCF₃ 76 CF₃CF₂CH₂ 5-NO₂ 64 CF₃CF₂CH₂ 5-CN 77 CF₃CF₂CH₂3-OMe

Present Compound 15

¹H-NMR (CDCl₃) δ: 8.43 (1H, d), 7.54 (1H, d), 7.38 (1H, d), 7.31 (1H,dd), 6.94 (1H, d), 6.78 (1H, dd), 4.52 (2H, t), 3.86 (3H, s), 2.85 (2H,q), 1.25 (3H, t).

Present Compound 25

¹H-NMR (CDCl₃) δ: 8.44 (1H, d), 7.78-7.75 (2H, m), 7.67-7.64 (1H, m),7.53-7.48 (1H, m), 7.35 (1H, dd), 4.55 (2H, td), 2.32 (2H, q), 0.93 (3H,t).

Present Compound 71

¹H-NMR (CDCl₃) δ: 8.47 (1H, dd), 7.60-7.47 (4H, m), 7.37 (1H, dd), 4.54(2H, td), 2.91 (2H, q), 1.28 (3H, t).

Present Compound 72

¹H-NMR (CDCl₃) δ: 8.49 (1H, d), 7.43-7.28 (4H, m), 7.12-7.08 (1H, m),4.54 (2H, t), 2.83 (2H, d), 1.25 (3H, t).

Present Compound 73

¹H-NMR (CDCl₃) δ: 8.46 (1H, dd), 7.52-7.44 (2H, m), 7.39-7.34 (3H, m),4.54 (2H, t), 2.86 (2H, dd), 1.26 (3H, t).

Present Compound 31

¹H-NMR (CDCl₃) δ: 8.49 (1H, d), 8.20 (1H, d), 8.05 (1H, dd), 7.62 (1H,d), 7.59 (1H, d), 7.39 (1H, dd), 4.55 (2H, td), 2.99 (2H, q), 1.33 (3H,t).

Present Compound 47

¹H-NMR (CDCl₃) δ: 8.45 (1H, d), 7.55 (1H, d), 7.44 (1H, d), 7.35 (1H,dd), 7.20-7.18 (1H, m), 7.10-7.07 (1H, m), 4.53 (2H, t), 2.88 (2H, q),1.28 (3H, t).

Present Compound 74

378 (M+H)

Present Compound 56

¹H-NMR (CDCl₃) δ: 8.44 (1H, d), 7.54 (1H, d), 7.48 (1H, d), 7.38-7.32(2H, m), 7.29 (1H, d), 4.53 (2H, td), 2.87 (2H, q), 1.26 (3H, td).

Present Compound 75

¹H-NMR (CDCl₃) δ: 8.46 (1H, dd), 7.59 (1H, dd), 7.41 (1H, d), 7.35 (1H,dd), 7.33-7.32 (1H, m), 7.23-7.19 (1H, m), 4.54 (2H, td), 2.84 (2H, q),1.24 (3H, t).

Present Compound 76

¹H-NMR (CDCl₃) δ: 8.49 (1H, t), 8.27 (1H, d), 8.19 (1H, dd), 7.60 (1H,dd), 7.43-7.38 (2H, m), 4.56 (2H, td), 3.01 (2H, q), 1.35 (3H, t).

Present Compound 64

¹H-NMR (CDCl₃) δ: 8.47 (1H, dd), 7.67-7.66 (1H, m), 7.59 (1H, dd), 7.55(1H, dd), 7.40-7.36 (2H, m), 4.55 (2H, td), 2.95 (2H, q), 1.32 (3H, t).

Present Compound 77

¹H-NMR (CDCl₃) δ: 8.41 (1H, d), 7.49 (1H, d), 7.36 (1H, t), 7.32 (1H,dd), 7.10 (1H, dd), 6.96 (1H, dd), 4.53 (2H, t), 3.95 (3H, s), 2.68 (2H,q), 1.00 (3H, t).

Preparation Example 3

To a mixture of the Intermediate compound 5 (2.0 g), triisopropyl borate(2.4 mL), toluene (20 mL), and THE (6.6 mL) was added dropwise a 2.6 Mn-butyllithium solution in hexane (4 mL) under nitrogen atmosphere at−78° C. The reaction mixture was stirred at −78° C. for 1 hour and thenallowed to stand to room temperature, and to the mixture were added a 2M sodium carbonate aqueous solution (12 mL) and the Intermediatecompound 1 (2.3 g). To the mixture was addedtetrakistriphenylphosphinepalladium(0) (920 mg), and then the mixturewas stirred at 95° C. for 6 hours. The resulting reaction mixture wasallowed to stand to room temperature, and to the mixture was addedwater, and the mixture was extracted with ethyl acetate. The resultingorganic layers were dried over anhydrous sodium sulfate, and the organiclayers were concentrated under reduced pressure. The resulting residueswere subjected to silica gel chromatography to give the Present compound12 represented by the following formula (2.4 g).

The compounds prepared according to the process described in thePreparation Example 3 and the physical properties thereof are shownbelow.

The compounds represented by formula (I-2)

[wherein the number on the benzene ring represents the binding positionof each substituent.]wherein R¹ and (R³)_(q) represent any one combination indicated in Table9.

TABLE 9 Present compound R¹ (R³)_(q) 12 CF₃CF₂CH₂ 4-Cl 21 CF₃CF₂CH₂ 5-Cl28 CF₃CF₂CH₂ 3-Cl 50 CF₃CF₂CH₂ 4-Me 44 CF₃CF₂CH₂ 5-Me 78 CF₃CF₂CH₂ 6-Me35 CF₃CF₂CH₂ 6-OMe

Present Compound 12

¹H-NMR (CDCl₃) δ: 8.44 (1H, d), 7.54 (1H, d), 7.37-7.32 (3H, m), 7.21(1H, dd), 4.52 (2H, td), 2.87 (2H, q), 1.27 (3H, t).

Present Compound 21

¹H-NMR (CDCl₃) δ: 8.45 (1H, d), 7.57 (1H, d), 7.44 (1H, t), 7.36-7.31(3H, m), 4.53 (2H, t), 2.82 (2H, q), 1.22 (3H, t).

Present Compound 28

¹H-NMR (CDCl₃) δ: 8.41 (1H, dd), 7.55-7.50 (2H, m), 7.40-7.30 (3H, m),4.54 (2H, td), 2.63 (2H, q), 1.00 (3H, t).

Present Compound 50

¹H-NMR (CDCl₃) δ: 8.44 (1H, dd), 7.55 (1H, dd), 7.34-7.30 (2H, m), 7.22(1H, s), 7.07-7.05 (1H, m), 4.52 (2H, td), 2.83 (2H, q), 2.39 (3H, s),1.23 (3H, t).

Present Compound 44

¹H-NMR (CDCl₃) δ: 8.44 (1H, d), 7.58 (1H, d), 7.35-7.31 (2H, m), 7.28(1H, d), 7.18-7.15 (1H, m), 4.52 (2H, t), 2.77 (2H, q), 2.36 (3H, s),1.19 (3H, t).

Present Compound 78

¹H-NMR (CDCl₃) δ: 8.47 (1H, d), 7.36 (1H, dd), 7.29-7.20 (3H, m), 7.09(1H, dt), 4.54 (2H, t), 2.79 (2H, q), 2.04 (3H, s), 1.22 (3H, t).

Present Compound 35

¹H-NMR (CDCl₃) δ: 8.47 (1H, dd), 7.36-7.29 (3H, m), 6.99 (1H, dd), 6.80(1H, dd), 4.52 (2H, td), 3.72 (3H, s), 2.82 (2H, q), 1.23 (3H, t).

The compound prepared according to the process described in thePreparation Example 3 and the physical property thereof are shown below.

The compound represented by formula (I-3)

[wherein the number on the benzene ring represents the binding positionof each substituent.]wherein R¹ represents a CF₃CF₂CH₂ group, X represents a fluorine atom,and (R³)_(q) represents a 4-OCF₃ group (Intermediate compound 18).

Intermediate Compound 18

¹H-NMR (CDCl₃) δ: 8.47 (1H, d), 8.03 (1H, t), 7.80-7.77 (1H, m), 7.35(1H, dd), 7.15-7.13 (1H, m), 7.08-7.05 (1H, m), 4.53 (2H, t).

Preparation Example 4

To a mixed solution of the Present compound 1 (0.72 g) and ethyl acetate(5 mL) was added dropwise a mixture of mCPBA (70%) (0.68 g) and ethylacetate (1.7 mL) under ice-cooling. The mixture was stirred underice-cooling for 4 hours, and then to the mixture were sequentially addeda saturated sodium thiosulfate aqueous solution and a saturated sodiumhydrogen carbonate aqueous solution, and the mixture was extracted withethyl acetate. The resulting organic layers were dried over anhydroussodium sulfate, and concentrated under reduced pressure. The resultingresidues were subjected to silica gel chromatography to give the Presentcompound 2 represented by the following formula (0.23 g) and the Presentcompound 3 represented by the following formula (0.41 g).

The compounds prepared according to the process described in thePreparation Example 4 and the physical properties thereof are shownbelow.

The compounds represented by formula (I-1)

[wherein the number on the benzene ring represents the binding positionof each substituent.]wherein R¹, (R³)_(q), and n represent any one combination indicated inTable 10.

TABLE 10 Present compound R¹ (R³)_(q) n 2 CF₃CF₂CH₂ H 1 3 CF₃CF₂CH₂ H 25 CF₂HCF₂CH₂ H 1 6 CF₂HCF₂CH₂ H 2 13 CF₃CF₂CH₂ 4-Cl 1 14 CF₃CF₂CH₂ 4-Cl2 16 CF₃CF₂CH₂ 4-OCH₃ 1 17 CF₃CF₂CH₂ 4-OCH₃ 2 19 CF₃CF₂CH₂ 5-CF₃ 1 20CF₃CF₂CH₂ 5-CF₃ 2 22 CF₃CF₂CH₂ 5-Cl 1 23 CF₃CF₂CH₂ 5-Cl 2 26 CF₃CF₂CH₂3-CF₃ 1 27 CF₃CF₂CH₂ 3-CF₃ 2 29 CF₃CF₂CH₂ 3-Cl 1 30 CF₃CF₂CH₂ 3-Cl 2 41CF₃CF₂CH₂ 4-CF₃ 1 39 CF₃CF₂CH₂ 6-CF₃ 2 52 CF₃CF₂CH₂ 4-Me 2 51 CF₃CF₂CH₂4-Me 1 46 CF₃CF₂CH₂ 5-Me 2 45 CF₃CF₂CH₂ 5-Me 1 37 CF₃CF₂CH₂ 6-OMe 2 36CF₃CF₂CH₂ 6-OMe 1 43 CF₃CF₂CH₂ 6-Me 2 32 CF₃CF₂CH₂ 4-NO₂ 2 49 CF₃CF₂CH₂4-OCF₃ 2 48 CF₃CF₂CH₂ 4-OCF₃ 1 42 CF₃CF₂CH₂ 6-Cl 2 40 CF₃CF₂CH₂ 3-Me 258 CF₃CF₂CH₂ 4-Br 2 57 CF₃CF₂CH₂ 4-Br 1 55 CF₃CF₂CH₂ 5-OCF₃ 2 54CF₃CF₂CH₂ 5-OCF₃ 1 34 CF₃CF₂CH₂ 5-NO₂ 2 33 CF₃CF₂CH₂ 5-NO₂ 1 66CF₃CF₂CH₂ 5-CN 2 65 CF₃CF₂CH₂ 5-CN 1 38 CF₃CF₂CH₂ 3-OMe 2

Present Compound 2

¹H-NMR (CDCl₃) δ: 8.40 (1H, d), 8.26 (1H, dd), 7.71 (1H, d), 7.67-7.61(2H, m), 7.58-7.53 (1H, m), 7.40 (1H, dd), 4.55 (2H, td), 3.48-3.38 (1H,m), 2.92-2.83 (1H, m), 1.40 (3H, t).

Present Compound 3

¹H-NMR (CDCl₃) δ: 8.37 (1H, d), 8.16 (1H, dd), 7.70 (1H, td), 7.61 (1H,td), 7.48 (1H, dd), 7.44 (1H, dd), 7.36 (1H, dd), 4.53 (2H, td), 3.44(2H, q), 1.27 (3H, t).

Present Compound 5

¹H-NMR (CDCl₃) δ: 8.40 (1H, d), 8.25 (1H, dd), 7.70 (1H, d), 7.67-7.61(2H, m), 7.55 (1H, td), 7.39 (1H, dd), 6.23-5.94 (1H, m), 4.49 (2H, t),3.48-3.38 (1H, m), 2.92-2.82 (1H, m), 1.39 (3H, t).

Present Compound 6

¹H-NMR (CDCl₃) δ: 8.35 (1H, dd), 8.15 (1H, dd), 7.69 (1H, td), 7.61 (1H,td), 7.48 (1H, dd), 7.44 (1H, dd), 7.35 (1H, dd), 6.23-5.94 (1H, m),4.46 (2H, dd), 3.44 (2H, q), 1.27 (3H, t).

Present Compound 13

¹H-NMR (CDCl₃) δ: 8.40 (1H, d), 8.24 (1H, d), 7.70 (1H, d), 7.62 (1H,d), 7.51 (1H, dd), 7.40 (1H, dd), 4.55 (2H, td), 3.50-3.40 (1H, m),2.92-2.83 (1H, m), 1.41 (3H, t).

Present Compound 14

¹H-NMR (CDCl₃) δ: 8.36 (1H, dd), 8.15 (1H, d), 7.66 (1H, dd), 7.46 (1H,dd), 7.39 (1H, d), 7.36 (1H, dd), 4.53 (2H, td), 3.47 (2H, q), 1.29 (3H,t).

Present Compound 16

¹H-NMR (CDCl₃) δ: 8.36 (1H, d), 7.81 (1H, d), 7.64 (1H, d), 7.61 (1H,d), 7.37 (1H, dd), 7.06 (1H, dd), 4.53 (2H, td), 3.95 (3H, s), 3.49-3.39(1H, m), 2.88-2.79 (1H, m), 1.41 (3H, t).

Present Compound 17

¹H-NMR (CDCl₃) δ: 8.35 (1H, d), 7.67 (1H, d), 7.45 (1H, d), 7.38-7.32(2H, m), 7.19 (1H, dd), 4.52 (2H, dd), 3.92 (3H, s), 3.43 (2H, q), 1.26(3H, t).

Present Compound 19

¹H-NMR (CDCl₃) δ: 8.44-8.43 (1H, m), 8.41 (1H, d), 7.92 (1H, br s),7.89-7.86 (1H, m), 7.80-7.77 (1H, m), 7.44 (1H, dd), 4.57 (2H, td),3.52-3.42 (1H, m), 2.95-2.85 (1H, m), 1.41 (3H, t).

Present Compound 20

¹H-NMR (CDCl₃) δ: 8.39-8.38 (1H, m), 8.30 (1H, d), 7.87 (1H, dd),7.71-7.70 (1H, m), 7.52 (1H, dd,), 7.40 (1H, dd), 4.54 (2H, td), 3.49(2H, q), 1.29 (3H, t).

Present Compound 22

¹H-NMR (CDCl₃) δ: 8.41 (1H, t), 8.20 (1H, dd), 7.71 (1H, dd), 7.65 (1H,t), 7.60 (1H, dt), 7.41 (1H, dt), 4.56 (2H, t), 3.48-3.38 (1H, m),2.93-2.83 (1H, m), 1.39 (3H, t).

Present Compound 23

¹H-NMR (CDCl₃) δ: 8.37 (1H, dd), 8.09 (1H, d), 7.58 (1H, dd), 7.48 (1H,dd), 7.44 (1H, d), 7.37 (1H, dd), 4.53 (2H, td), 3.44 (2H, q), 1.26 (3H,t).

Present Compound 26

¹H-NMR (CDCl₃) δ: 8.36 (1H, d), 7.86-7.83 (1H, m), 7.64 (1H, t),7.56-7.53 (1H, m), 7.49-7.45 (1H, m), 7.34 (1H, dd), 4.53 (2H, td),3.82-3.73 (1H, m), 3.10-3.00 (1H, m), 1.32 (3H, t).

Present Compound 27

¹H-NMR (CDCl₃) δ: 8.32-8.31 (1H, m), 8.00-7.96 (1H, m), 7.76 (1H, t),7.61-7.58 (1H, m), 7.47-7.44 (1H, m), 7.38 (1H, dd), 4.53 (2H, td),3.78-3.68 (2H, br m), 1.38 (3H, t).

Present Compound 29

¹H-NMR (CDCl₃) δ: 8.36 (1H, d), 7.50 (2H, dd), 7.44 (1H, t), 7.36-7.33(2H, m), 4.56-4.50 (2H, m), 3.82-3.73 (1H, m), 3.46-3.36 (1H, m), 1.43(3H, t).

Present Compound 30

¹H-NMR (CDCl₃) δ: 8.32 (1H, d), 7.63 (1H, dd), 7.54 (1H, t), 7.39-7.36(1H, m), 7.34-7.29 (2H, m), 4.51 (2H, t), 3.55 (2H, q), 1.35 (3H, t).

Present Compound 41

¹H-NMR (CDCl₃) δ: 8.56 (1H, s), 8.44 (1H, d), 7.82-7.79 (2H, m), 7.77(1H, d), 7.44 (1H, dd), 4.57 (2H, td), 3.53-3.43 (1H, m), 2.94-2.86 (1H,m), 1.42 (3H, t).

Present Compound 39

¹H-NMR (CDCl₃) δ: 8.38-8.37 (2H, m), 8.07 (1H, d), 7.77 (1H, dd), 7.43(1H, d), 7.35 (1H, dd), 4.54 (2H, t), 3.28-3.13 (2H, m), 1.21 (3H, t).

Present Compound 52

¹H-NMR (CDCl₃) δ: 8.36-8.35 (1H, m), 7.96 (1H, s), 7.50-7.45 (2H, m),7.36-7.31 (2H, m), 4.52 (2H, t), 3.43 (2H, dd), 2.50 (3H, s), 1.27 (3H,t).

Present Compound 51

¹H-NMR (CDCl₃) δ: 8.38 (1H, d), 8.05 (1H, d), 7.67 (1H, d), 7.56 (1H,d), 7.39-7.33 (2H, m), 4.54 (2H, td), 3.46-3.41 (1H, m), 2.86-2.82 (1H,m), 2.50 (3H, s), 1.40 (3H, t).

Present Compound 46

¹H-NMR (CDCl₃) δ: 8.36 (1H, dd), 8.02 (1H, d), 7.48 (1H, dd), 7.41-7.39(1H, m), 7.35 (1H, dd), 7.25-7.23 (1H, m), 4.52 (2H, t), 3.37 (2H, q),2.48 (3H, s), 1.24 (3H, t).

Present Compound 45

¹H-NMR (CDCl₃) δ: 8.39 (1H, dd), 8.12 (1H, d), 7.69 (1H, dd), 7.46-7.42(2H, m), 7.39 (1H, dd), 4.54 (2H, t), 3.43-3.34 (1H, m), 2.89-2.80 (1H,m), 2.48 (3H, s), 1.37 (3H, t).

Present Compound 37

¹H-NMR (CDCl₃) δ: 8.37 (1H, d), 7.74 (1H, dd), 7.56 (1H, t), 7.39 (1H,d), 7.34 (1H, dd), 7.26 (1H, d), 4.52 (2H, t), 3.77 (3H, s), 3.22 (2H,d), 1.21 (3H, t).

Present Compound 36

¹H-NMR (CDCl₃) δ: 8.39 (1H, dd), 7.75 (1H, dd), 7.64-7.62 (1H, m), 7.59(1H, t), 7.34 (1H, dd), 7.10 (1H, dd), 4.54 (2H, td), 3.83 (3H, s),3.33-3.25 (1H, m), 2.86-2.77 (1H, m), 1.31 (3H, t).

Present Compound 43

¹H-NMR (CDCl₃) δ: 8.40 (1H, dd), 8.00-7.98 (1H, m), 7.57-7.56 (1H, m),7.50 (1H, t), 7.37 (2H, d), 4.54 (2H, td), 3.10-3.02 (2H, m), 2.05 (3H,s), 1.17 (3H, t).

Present Compound 32

¹H-NMR (CDCl₃) δ: 9.02 (1H, d), 8.53 (1H, dd), 8.41 (1H, d), 7.67 (1H,d), 7.53 (1H, d), 7.41 (1H, dd), 4.55 (2H, t), 3.58 (2H, q), 1.33 (3H,t).

Present Compound 49

¹H-NMR (CDCl₃) δ: 8.37 (1H, dd), 8.03 (1H, d), 7.57-7.46 (3H, m), 7.38(1H, dd), 4.53 (2H, td), 3.48 (2H, q), 1.28 (3H, t).

Present Compound 48

¹H-NMR (CDCl₃) δ: 8.41 (1H, d), 8.14 (1H, d), 7.73 (1H, d), 7.71 (1H,d), 7.43-7.38 (2H, m), 4.56 (2H, t), 3.50-3.40 (1H, m), 2.93-2.84 (1H,m), 1.39 (3H, t).

Present Compound 42

¹H-NMR (CDCl₃) δ: 8.40 (1H, d), 8.09-8.07 (1H, m), 7.78 (1H, dd), 7.56(1H, t), 7.45-7.36 (2H, m), 4.54 (2H, t), 3.30-3.10 (2H, m), 1.21 (3H,t).

Present Compound 40

¹H-NMR (CDCl₃) δ: 8.28 (1H, dd), 7.48 (1H, t), 7.39-7.30 (3H), 7.18 (1H,dd), 4.50 (2H, td), 3.43 (2H, q), 2.78 (3H, s), 1.33 (3H, t).

Present Compound 58

¹H-NMR (CDCl₃) δ: 8.37 (1H, dd), 8.30 (1H, d), 7.82 (1H, dd), 7.46 (1H,dd), 7.36 (1H, dd), 7.32 (1H, d), 4.53 (2H, td), 3.47 (2H, q), 1.29 (3H,t).

Present Compound 57

¹H-NMR (CDCl₃) δ: 8.40-8.33 (2H, m), 7.70-7.60 (2H, m), 7.56-7.51 (1H,m), 7.43-7.38 (1H, m), 4.56 (2H, td), 3.50-3.40 (1H, m), 2.91-2.82 (1H,m), 1.41 (3H, t).

Present Compound 55

¹H-NMR (CDCl₃) δ: 8.38 (1H, d), 8.21 (1H, d), 7.49 (1H, dd), 7.45-7.41(1H, m), 7.38 (1H, dd), 7.28-7.26 (1H, m), 4.54 (2H, t), 3.47 (2H, q),1.28 (3H, t).

Present Compound 54

¹H-NMR (CDCl₃) δ: 8.42 (1H, d), 8.30 (1H, d), 7.71 (1H, d), 7.51-7.45(2H, m), 7.42 (1H, dd), 4.56 (2H, t), 3.50-3.41 (1H, m), 2.94-2.85 (1H,m), 1.40 (3H, t).

Present Compound 34

¹H-NMR (CDCl₃) δ: 8.43-8.36 (3H, m), 8.30 (1H, d), 7.56 (1H, d), 7.42(1H, dd), 4.55 (2H, t), 3.55 (2H, q), 1.31 (3H, t).

Present Compound 33

¹H-NMR (CDCl₃) δ: 8.56 (1H, d), 8.49-8.41 (3H, m), 7.88 (1H, d), 7.49(1H, dd), 4.59 (2H, td), 3.56-3.47 (1H, m), 2.99-2.90 (1H, m), 1.43 (3H,t).

Present Compound 66

¹H-NMR (CDCl₃) δ: 8.39 (1H, d), 8.29 (1H, d), 7.89 (1H, dd), 7.75 (1H,d), 7.50 (1H, d), 7.40 (1H, dd), 4.54 (2H, t), 3.50 (2H, q), 1.29 (3H,t).

Present Compound 65

¹H-NMR (CDCl₃) δ: 8.45-8.43 (1H, m), 8.40 (1H, d), 7.97 (1H, d), 7.89(1H, dd), 7.76 (1H, d), 7.45 (1H, dd), 4.57 (2H, td), 3.52-3.43 (1H, m),2.94-2.85 (1H, m), 1.41 (3H, t).

Present Compound 38

¹H-NMR (CDCl₃) δ: 8.33 (1H, dd), 7.58 (1H, dd), 7.37 (1H, dd), 7.28 (1H,dd), 7.13 (1H, dd), 6.99 (1H, dd), 4.50 (2H, td), 4.03 (3H, s),3.44-3.39 (2H, m), 1.26 (3H, t).

Preparation Example 5

To a mixed solution of the Present compound 28 (0.50 g) and ethylacetate (3 mL) was added dropwise a mixture of mCPBA (70%) (1.2 g) andethyl acetate (1.2 mL) under ice-cooling. The mixture was stirred underice-cooling for 6 hours, and then to the mixture were sequentially addeda saturated sodium thiosulfate aqueous solution and a saturated sodiumhydrogen carbonate aqueous solution, and the mixture was extracted withethyl acetate. The resulting organic layers were dried over sodiumsulfate, and concentrated under reduced pressure. The resulting residueswere subjected to silica gel chromatography to give the Present compound10 represented by the following formula (0.33 g).

Present Compound 10

¹H-NMR (CDCl₃) δ: 8.03 (1H, d), 7.70 (1H, dd), 7.61 (1H, t), 7.27 (1H,d), 7.20 (1H, dd), 7.01 (1H, dd), 4.48 (2H, td), 4.04-3.97 (1H, m),3.62-3.52 (1H, m), 1.43 (3H, t).

Preparation Example 6

To a mixture of the Intermediate compound 1 (1.0 g),2-fluoro-4-methoxyphenylboronic acid (0.50 g), a 2 M sodium carbonateaqueous solution (4.4 mL), and 1,2-dimethoxyethane (9.8 mL) was addedtetrakistriphenylphosphinepalladium(0) (340 mg) under nitrogenatmosphere at room temperature. The resulting mixture was stirred at 80°C. for 5 hours. The resulting reaction mixture was allowed to stand toroom temperature, and to the mixture was added water, and the mixturewas extracted with ethyl acetate. The resulting organic layers weredried over anhydrous sodium sulfate, and the organic layers wereconcentrated under reduced pressure. The resulting residues weresubjected to silica gel chromatography to give the Intermediate compound8 represented by the following formula (0.96 g).

The compounds prepared according to the process described in thePreparation Example 6 and the physical properties thereof are shownbelow.

The compounds represented by formula (C-1)

[wherein the number on the benzene ring represents the binding positionof each substituent.]wherein R¹ and (R³)_(q) represent any one combination indicated in Table11.

TABLE 11 Intermediate compound R¹ (R³)_(q) 8 CF₃CF₂CH₂ 4-OCH₃ 9CF₃CF₂CH₂ 5-CF₃ 10 CF₃CF₂CH₂ 3-CF₃ 15 CF₃CF₂CH₂ 6-CF₃ 16 CF₃CF₂CH₂ 6-Cl17 CF₃CF₂CH₂ 3-Me 19 CF₃CF₂CH₂ 4-NO₂ 22 CF₃CF₂CH₂ 5-OCF₃ 23 CF₃CF₂CH₂5-NO₂ 24 CF₃CF₂CH₂ 5-CN 25 CF₃CF₂CH₂ 3-OMe 26 CF₃CF₂CH₂ 4-CF₃

Intermediate Compound 8

¹H-NMR (CDCl₃) δ: 8.43 (1H, d), 7.90 (1H, t), 7.74 (1H, dt), 7.32 (1H,dd), 6.82 (1H, dd), 6.70 (1H, dd), 4.51 (2H, t), 3.85 (3H, s).

Intermediate Compound 9

¹H-NMR (CDCl₃) δ: 8.50 (1H, d), 8.33 (1H, dd), 7.85-7.82 (1H, m),7.65-7.61 (1H, m), 7.36 (1H, dd), 7.30-7.25 (1H, m), 4.54 (2H, td).

Intermediate Compound 10

¹H-NMR (CDCl₃) δ: 8.49 (1H, d), 8.21-8.16 (1H, m), 7.84-7.81 (1H, m),7.66-7.62 (1H, m), 7.38-7.34 (2H, m), 4.54 (2H, td).

Intermediate Compound 15

¹H-NMR (CDCl₃) δ: 8.46 (1H, dd), 7.60-7.49 (2H, m), 7.39-7.34 (3H, m),4.54 (2H, td).

Intermediate Compound 16

¹H-NMR (CDCl₃) δ: 8.50 (1H, d), 7.43-7.29 (4H, m), 7.13-7.08 (1H, m),4.54 (2H, t).

Intermediate Compound 17

¹H-NMR (CDCl₃) δ: 8.46 (1H, d), 7.76 (1H, dd), 7.70 (1H, td), 7.33 (1H,dd), 7.24-7.19 (1H, m), 7.14 (1H, t), 4.52 (2H, t), 2.35 (3H, s).

Intermediate Compound 19

¹H-NMR (CDCl₃) δ: 8.52 (1H, d), 8.26 (1H, t), 8.16-8.13 (1H, m), 8.05(1H, dd), 7.93-7.90 (1H, m), 7.38 (1H, dd), 4.56 (2H, td).

Intermediate Compound 22

¹H-NMR (CDCl₃) δ: 8.48 (1H, d), 7.93-7.91 (1H, m), 7.85-7.83 (1H, m),7.35 (1H, dd), 7.22-7.15 (2H, m), 4.54 (2H, td).

Intermediate Compound 23

¹H-NMR (CDCl₃) δ: 8.99 (1H, dd), 8.52 (1H, d), 8.26 (1H, ddd), 7.88-7.85(1H, m), 7.38 (1H, dd), 7.32 (1H, dd), 4.56 (2H, td).

Intermediate Compound 24

¹H-NMR (CDCl₃) δ: 8.49 (1H, d), 8.41 (1H, dd), 7.85-7.82 (1H, m), 7.66(1H, dq), 7.37 (1H, dd), 7.30-7.25 (1H, m), 4.55 (2H, t).

Intermediate Compound 25

¹H-NMR (CDCl₃) δ: 8.47 (1H, d), 7.80-7.77 (1H, m), 7.50-7.46 (1H, m),7.34 (1H, dd), 7.20-7.15 (1H, m), 7.03-6.98 (1H, m), 4.53 (2H, td), 3.94(3H, s).

Intermediate Compound 26

¹H-NMR (CDCl₃) δ: 8.50 (1H, d), 8.16-8.12 (1H, m), 7.86-7.83 (1H, m),7.54-7.51 (1H, m), 7.45-7.42 (1H, m), 7.36 (1H, dd), 4.54 (2H, td).

Preparation Example 7

To a mixture of the Present compound 23 (0.40 g) and methanol (2 mL) wasadded sodium methoxide (0.27 g) under nitrogen atmosphere at roomtemperature. The resulting reaction mixture was stirred at 80° C. for 10hours and then allowed to stand to room temperature, and to the mixturewas added a saturated ammonium chloride aqueous solution at roomtemperature. The resulting mixture was extracted with ethyl acetate, andthe organic layers were dried over anhydrous sodium sulfate. Theresulting organic layers were concentrated under reduced pressure. Theresulting residues were subjected to silica gel chromatography to givethe Present compound 24 represented by the following formula (80 mg).

Present Compound 24

¹H-NMR (CDCl₃) δ: 8.35 (1H, t), 8.06 (1H, d), 7.46 (1H, dd), 7.35 (1H,dd), 7.05 (1H, dd), 6.90 (1H, d), 4.52 (2H, td), 3.89 (3H, s), 3.39 (2H,q), 1.24 (3H, t).

Preparation Example 8

The Present compound 18 represented by the following formula (1.5 g) wasprepared by using the Intermediate compound 9 instead ofl-bromo-4-chloro-2-fluorobenzene according to the process described inthe Preparation Example 3.

Present Compound 18

¹H-NMR (CDCl₃) δ: 8.48 (1H, d), 7.66 (1H, d), 7.60-7.56 (2H, m), 7.44(1H, d), 7.37 (1H, dd), 4.54 (2H, t), 2.94 (2H, q), 1.30 (3H, t).

Preparation Example 9

The Intermediate compound 11 represented by the following formula wasprepared by using2-(2-fluoro-4-(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaninstead of the Intermediate compound 2 and using5-(benzyloxy)-2-chloropyridine instead of the Intermediate compound 1according to the process described in the Preparation Example 1.

Intermediate Compound 11

¹H-NMR (CDCl₃) δ: 8.51 (1H, d), 8.13 (1H, t), 7.79 (1H, dd), 7.52-7.33(8H, m), 5.18 (2H, s).

Preparation Example 10

The Intermediate compound 13 represented by the following formula (790mg) was prepared by using the Intermediate compound 12 instead of thePresent compound 1 according to the process described in the PreparationExample 4.

Intermediate Compound 13

¹H-NMR (CDCl₃) δ: 8.43 (1H, d), 8.40 (1H, d), 7.93 (1H, dd), 7.60 (1H,d), 7.49-7.36 (7H, m), 5.17 (2H, s), 3.51 (2H, q), 1.28 (3H, t).

Preparation Example 11

To a mixture of the Intermediate compound 13 (700 mg) and chloroform (25mL) was added boron tribromide (a 2 M solution in dichloromethane) (2.8mL) at −20° C. The resulting reaction mixture was stirred underice-cooling for 1 hour. To the reaction mixture was added water, and themixture was sequentially extracted with chloroform and ethyl acetate.The combined organic layers were dried over anhydrous sodium sulfate,and concentrated under reduced pressure. The resulting residues weresubjected to silica gel chromatography to give the Intermediate compound14 represented by the following formula (430 mg).

Intermediate Compound 14

¹H-NMR (CDCl₃) δ: 8.43 (1H, d), 8.23 (1H, dd), 7.94 (1H, dd), 7.61 (1H,d), 7.37 (1H, d), 7.18 (1H, dd), 5.96 (1H, s), 3.60 (2H, q), 1.32 (3H,t).

Preparation Example 12

To a mixture of the Intermediate compound 14 (140 mg), cesium carbonate(170 mg), and NMP (3 mL) was added2,2,2-trifluoroethyl=nonafluorobutylsulfonate (180 mg) underice-cooling. The resulting reaction mixture was stirred at roomtemperature for 1.5 hours. To the reaction mixture was added water, andthe mixture was extracted with ethyl acetate. The resulting organiclayers were sequentially washed with water and saturated brine, anddried over anhydrous sodium sulfate. The organic layers wereconcentrated under reduced pressure to give the Present compound 7represented by the following formula (150 mg).

The compounds prepared according to the process described in thePreparation Example 12 and the physical properties thereof are shownbelow.

The compounds represented by formula (I-1)

[wherein the number on the benzene ring represents the binding positionof each substituent.]wherein R¹, (R³)_(q), and n represent any one combination indicated inTable 12.

TABLE 12 Present compound R¹ (R³)_(q) n 7 CF₃CH₂ 4-CF₃ 2 8 CF₃CF₂CH₂4-CF₃ 2 9 CF₃CFHCF₂CH₂ 4-CF₃ 2 11 CF₂HCF₂CH₂ 4-CF₃ 2

Present Compound 7

¹H-NMR (CDCl₃) δ: 8.43 (1H, d), 8.39 (1H, dd), 7.95 (1H, dd), 7.60 (1H,d), 7.50 (1H, dd), 7.39 (1H, dd), 4.48 (2H, q), 3.52 (2H, q), 1.30 (3H,t).

Present Compound 8

¹H-NMR (CDCl₃) δ: 8.43 (1H, d), 8.39 (1H, dd), 7.95 (1H, dd), 7.60 (1H,d), 7.50 (1H, dd), 7.39 (1H, dd), 4.54 (2H, td), 3.51 (2H, q), 1.30 (3H,t).

Present Compound 9

¹H-NMR (CDCl₃) δ: 8.43 (1H, d), 8.38 (1H, dd), 7.95 (1H, dd), 7.60 (1H,d), 7.50 (1H, dd), 7.39 (1H, dd), 5.32-5.10 (1H, m), 4.58-4.36 (2H, m),3.51 (2H, q), 1.30 (3H, t).

Present Compound 11

¹H-NMR (CDCl₃) δ: 8.43 (1H, d), 8.38 (1H, d), 7.95 (1H, dd), 7.60 (1H,d), 7.50 (1H, d), 7.38 (1H, dd), 6.09 (1H, tt), 4.48 (2H, t), 3.52 (2H,q), 1.30 (3H, t).

Preparation Example 13

A mixture of the Present compound 32 (2.17 g), palladium carbon (10%palladium) (0.22 g), and ethyl acetate (12 mL) was stirred underhydrogen atmosphere at 35° C. for 6 hours. The resulting reactionmixture was filtered through Celite, and the filtrate was concentratedunder reduced pressure to give the Present compound 53 represented bythe following formula (2.00 g).

Present Compound 53

¹H-NMR (CDCl₃) δ: 8.33 (1H, d), 7.44-7.41 (2H, m), 7.31 (1H, dd), 7.21(1H, d), 6.91 (1H, dd), 4.51 (2H, td), 4.03 (2H, br s), 3.42 (2H, q),1.26 (3H, t).

The compounds prepared according to the process described in thePreparation Example 13 and the physical properties thereof are shownbelow.

Present Compound 62

¹H-NMR (CDCl₃) δ: 8.34 (1H, d), 7.88 (1H, d), 7.47-7.44 (1H, m), 7.33(1H, dd), 6.74 (1H, dd), 6.59 (1H, d), 4.51 (2H, td), 4.21 (2H, br s),3.30 (2H, q), 1.23 (3H, t).

Intermediate Compound 20

¹H-NMR (CDCl₃) δ: 8.40 (1H, d), 7.77 (1H, t), 7.70 (1H, dd), 7.29 (1H,dd), 6.56 (1H, dd), 6.44 (1H, dd), 4.50 (2H, td), 3.90 (2H, br s).

Preparation Example 14

To a mixture of the Present compound 53 (0.30 g) and pyridine (2 mL) wasadded cyclopropanecarbonyl chloride (0.11 mL) under ice-cooling. Theresulting reaction mixture was stirred at room temperature for 3 hours.To the reaction mixture was added water, and the mixture was extractedwith ethyl acetate. The resulting organic layers were sequentiallywashed with saturated potassium hydrogen sulfate, water, and saturatedbrine, and dried over anhydrous sodium sulfate. The organic layers wereconcentrated under reduced pressure to give the Present compound 63represented by the following formula (0.35 g).

Present Compound 63

¹H-NMR (CDCl₃) δ: 8.37-8.34 (2H, m), 8.09 (1H, br s), 7.98 (1H, d), 7.46(TH, dd), 7.41 (1H, d), 7.34 (1H, dd), 4.54-4.48 (2H, m), 3.56 (2H, q),1.62-1.54 (1H, m), 1.30 (3H, t), 1.14-1.10 (2H, m), 0.91-0.88 (2H, m).

Preparation Example 15

A mixture of sodium nitrite (0.41 g) and (6.7 mL) was added to a mixtureof the Intermediate compound 20 (8.58 g) and 48% hydrobromic acid (6.7mL) under ice-cooling. The resulting reaction mixture was stirred atroom temperature for 15 minutes. To the reaction mixture was addedcopper(I) bromide (0.37 g) under ice-cooling, and the mixture wasstirred for 15 minutes. The resulting reaction mixture was stirred atroom temperature for 1 hour, and then warmed to 100° C., and stirred foradditional 1 hour. To the reaction mixture was added a saturatedpotassium carbonate aqueous solution at room temperature, and themixture was extracted with ethyl acetate. The resulting organic layerswere sequentially washed with water and saturated brine, and dried overanhydrous sodium sulfate. The resulting residues were subjected tosilica gel chromatography to give the Intermediate compound 21represented by the following formula (8.22 g).

Intermediate Compound 21

¹H-NMR (CDCl₃) δ: 8.46 (1H, d), 7.88 (1H, td), 7.79-7.76 (1H, m),7.42-7.39 (1H, m), 7.37-7.32 (2H, m), 4.53 (2H, td).

Preparation Example 16

To a mixture of the Present compound 56 (2.50 g) and NMP (28 mL) wereadded zinc cyanide (1.33 g) and tetrakistriphenylphosphinepalladium(0)(0.33 g). The resulting reaction mixture was stirred at 90° C. for 4hours, and then warmed to 180° C., and stirred for 1 hour. To thereaction mixture was added water at room temperature, and the mixturewas extracted with 2-methoxy-2-methylpropane. The resulting organiclayers were sequentially washed with water and saturated brine, anddried over anhydrous sodium sulfate. The resulting residues weresubjected to silica gel chromatography to give the Present compound 59represented by the following formula (0.10 g).

Present Compound 59

¹H-NMR (CDCl₃) δ: 8.48 (1H, d), 7.60-7.58 (2H, m), 7.54-7.49 (2H, m),7.37 (1H, dd), 4.54 (2H, t), 2.91 (2H, q), 1.29 (3H, dd).

The compound prepared according to the process described in thePreparation Example 16 and the physical properties thereof are shownbelow.

Present Compound 60

¹H-NMR (CDCl₃) δ: 8.47 (1H, d), 8.40 (1H, d), 7.97 (1H, dd), 7.59 (1H,d), 7.50 (1H, d), 7.40 (1H, dd), 4.54 (2H, t), 3.54 (2H, q), 1.31 (3H,t).

Preparation Example 17

To a mixture of the Present compound 60 (1.19 g) and water (0.8 mL) wasadded sulfuric acid (2.2 mL) under ice-cooling. The resulting reactionmixture was stirred at 130° C. for 30 minutes. To the reaction mixturewas added 10 M sodium hydroxide at room temperature, and the mixture wasextracted with ethyl acetate. The resulting organic layers weresequentially washed with 2 M dilute hydrochloric acid and saturatedbrine, and dried over anhydrous sodium sulfate. The resulting organiclayers were concentrated under reduced pressure to give the Presentcompound 61 represented by the following formula (1.02 g).

Present Compound 61

¹H-NMR (CDCl₃) δ: 8.49-8.49 (1H, m), 8.39-8.38 (1H, m), 8.25 (1H, dd),7.59-7.57 (1H, m), 7.51-7.49 (1H, m), 7.38 (1, dd), 4.54 (2H, td), 3.53(2H, q), 1.30 (3H, t).

Preparation Example 18

A mixture of the Present compound 58 (0.86 g), 1,2,4-triazole (0.38 g),copper(I) iodide (0.35 g), cesium carbonate (3.60 g), 8-hydroxyquinoline(0.21 g), water (1.4 mL), and DMF (12.5 mL) was stirred at 150° C. for 5hours. To the reaction mixture was added water at room temperature, andthe mixture was extracted with 2-methoxy-2-methylpropane. The resultingorganic layers were sequentially washed with water and saturated brine,and dried over anhydrous sodium sulfate. The resulting residues weresubjected to silica gel chromatography to give the Present compound 67represented by the following formula (0.08 g).

Present Compound 67

¹H-NMR (CDCl₃) δ: 8.73 (1H, s), 8.47 (1H, d), 8.40 (1H, d), 8.18 (1H,s), 8.09 (1H, dd), 7.63 (1H, d), 7.53 (1H, d), 7.39 (1H, dd), 4.55 (2H,t), 3.54 (2H, q), 1.32 (3H, t).

The compound prepared according to the process described in thePreparation Example 18 and the physical properties thereof are shownbelow.

Present Compound 70

¹H-NMR (CDCl₃) δ: 8.80 (1H, s), 8.48 (1H, d), 8.41 (1H, d), 8.12 (1H,dd), 7.67 (1H, d), 7.53 (1H, d), 7.40 (1H, dd), 4.55 (2H, t), 3.57 (2H,q), 1.33 (3H, t).

Preparation Example 19

To a mixture of the Present compound 58 (500 mg),4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane (402 mg),potassium acetate (309 mg), and DMSO (3.5 mL) was added[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (38 mg),and the mixture was stirred at 100° C. for 4.5 hours. To the reactionmixture was added water at room temperature, and the mixture wasextracted with 2-methoxy-2-methylpropane. The resulting organic layerswere sequentially washed with water and saturated brine, and dried overanhydrous sodium sulfate. The resulting residues were subjected tosilica gel chromatography to give the Intermediate compound 27represented by the following formula (454 mg).

Intermediate Compound 27

¹H-NMR (CDCl₃) δ: 8.56 (1H, d), 8.36 (1H, dd), 8.08 (1H, dd), 7.47 (1H,dd), 7.43 (1H, dd), 7.35 (1H, dd), 4.52 (2H, td), 3.46 (2H, q), 1.37(12H, s), 1.29 (3H, t).

Preparation Example 20

To a mixture of the Intermediate compound 27 (209 mg), 2-bromopyridine(127 mg), a 2 M sodium carbonate aqueous solution (0.6 mL), and1,2-dimethoxyethane (1.3 mL) was addedtetrakistriphenylphosphinepalladium(0) (46 mg) under nitrogen atmosphereat room temperature. The resulting mixture was stirred at 80° C. for 2hours. The resulting reaction mixture was allowed to stand to roomtemperature, and to the mixture was added water, and the mixture wasextracted with ethyl acetate. The resulting organic layers were driedover anhydrous sodium sulfate, and the organic layers were concentratedunder reduced pressure. The resulting residues were subjected to silicagel chromatography to give the Present compound 68 represented by thefollowing formula (113 mg).

Present Compound 68

¹H-NMR (CDCl₃) δ: 8.76-8.73 (2H, m), 8.42-8.39 (2H, m), 7.89-7.81 (2H,m), 7.57 (1H, d), 7.53 (1H, dd), 7.38 (1H, dd), 7.35-7.31 (1H, m), 4.54(2H, td), 3.53 (2H, q), 1.32 (3H, t).

The compound prepared according to the process described in thePreparation Example 20 and the physical properties thereof are shownbelow.

Present Compound 69

¹H-NMR (CDCl₃) δ: 9.01-9.00 (1H, m), 8.79 (1H, d), 8.45 (1H, dd),8.41-8.39 (1H, m), 8.07 (1H, dd), 8.00 (1H, d), 7.61 (1H, d), 7.55-7.53(1H, m), 7.39 (1H, dd), 4.55 (2H, t), 3.54 (2H, q), 1.32 (3H, t).

A compound represented by formula (100)

[wherein R³⁰¹, R³⁰², R³⁰³, R⁶⁰¹, R⁶⁰², R¹⁰⁰, and A¹ represent any onecombination indicated in the following Table 11 to Table 36.] may beprepared according to any one of the above processes.

TABLE 13 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 79 CF₂HCH₂H H NH₂ H H H 80 CF₂HCF₂CH₂ H H NH₂ H H H 81 CF₃CF₂CF₂CH₂ H H NH₂ H H H82 CF₃CFHCF₂CH₂ H H NH₂ H H H 83 CF₂HCH₂ H H NHCH₃ H H H 84 CF₃CF₂CH₂ HH NHCH₃ H H H 85 CF₂HCF₂CH₂ H H NHCH₃ H H H 86 CF₃CF₂CF₂CH₂ H H NHCH₃ HH H 87 CF₃CFHCF₂CH₂ H H NHCH₃ H H H 88 CF₂HCH₂ H H N(CH₃)₂ H H H 89CF₃CF₂CH₂ H H N(CH₃)₂ H H H 90 CF₂HCF₂CH₂ H H N(CH₃)₂ H H H 91CF₃CF₂CF₂CH₂ H H N(CH₃)₂ H H H 92 CF₃CFHCF₂CH₂ H H N(CH₃)₂ H H H 93CF₂HCH₂ H H N(CH₂CH₃)₂ H H H 94 CF₃CF₂CH₂ H H N(CH₂CH₃)₂ H H H 95CF₂HCF₂CH₂ H H N(CH₂CH₃)₂ H H H 96 CF₃CF₂CF₂CH₂ H H N(CH₂CH₃)₂ H H H 97CF₃CFHCF₂CH₂ H H N(CH₂CH₃)₂ H H H 98 CF₂HCH₂ H H NHCH₂CF₃ H H H 99CF₃CF₂CH₂ H H NHCH₂CF₃ H H H 100 CF₂HCF₂CH₂ H H NHCH₂CF₃ H H H 101CF₃CF₂CF₂CH₂ H H NHCH₂CF₃ H H H 102 CF₃CFHCF₂CH₂ H H NHCH₂CF₃ H H H

TABLE 14 Present com- pound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 103CF₂HCH₂ H H Cl H H H 104 CF₂HCF₂CH₂ H H Cl H H H 105 CF₃CF₂CF₂CH₂ H H ClH H H 106 CF₃CFHCF₂CH₂ H H Cl H H H 107 CF₂HCH₂ H Cl H H H H 108CF₂HCF₂CH₂ H Cl H H H H 109 CF₃CF₂CF₂CH₂ H Cl H H H H 110 CF₃CFHCF₂CH₂ HCl H H H H 111 CF₂HCH₂ H H OCH₃ H H H 112 CF₂HCF₂CH₂ H H OCH₃ H H H 113CF₃CF₂CF₂CH₂ H H OCH₃ H H H 114 CF₃CFHCF₂CH₂ H H OCH₃ H H H

TABLE 15 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 115 CF₂HCH₂H H

H H H 116 CF₃CF₂CH₂ H H

H H H 117 CF₂HCF₂CH₂ H H

H H H 118 CF₃CF₂CF₂CH₂ H H

H H H 119 CF₃CFHCF₂CH₂ H H

H H H 120 CF₂HCH₂ H H

H H H 121 CF₃CF₂CH₂ H H

H H H 122 CF₂HCF₂CH₂ H H

H H H 123 CF₃CF₂CF₂CH₂ H H

H H H 124 CF₃CFHCF₂CH₂ H H

H H H

TABLE 16 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 125 CF₂HCH₂H H

H H H 126 CF₃CF₂CH₂ H H

H H H 127 CF₂HCF₂CH₂ H H

H H H 128 CF₃CF₂CF₂CH₂ H H

H H H 129 CF₃CFHCF₂CH₂ H H

H H H 130 CF₂HCH₂ H H

H H H 131 CF₃CF₂CH₂ H H

H H H 132 CF₂HCF₂CH₂ H H

H H H 133 CF₃CF₂CF₂CH₂ H H

H H H 134 CF₃CFHCF₂CH₂ H H

H H H

TABLE 17 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 136 CF₂HCH₂H H

H H H 137 CF₃CF₂CH₂ H H

H H H 138 CF₂HCF₂CH₂ H H

H H H 139 CF₃CF₂CF₂CH₂ H H

H H H 140 CF₃CFHCF₂CH₂ H H

H H H 141 CF₂HCH₂ H H

H H H 142 CF₃CF₂CH₂ H H

H H H 143 CF₂HCF₂CH₂ H H

H H H 144 CF₃CF₂CF₂CH₂ H H

H H H 145 CF₃CFHCF₂CH₂ H H

H H H

TABLE 18 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 146 CF₂HCH₂H H

H H H 147 CF₃CF₂CH₂ H H

H H H 148 CF₂HCF₂CH₂ H H

H H H 149 CF₃CF₂CF₂CH₂ H H

H H H 150 CF₃CFHCF₂CH₂ H H

H H H 151 CF₂HCH₂ H H

H H H 152 CF₃CF₂CH₂ H H

H H H 153 CF₂HCF₂CH₂ H H

H H H 154 CF₃CF₂CF₂CH₂ H H

H H H 155 CF₃CFHCF₂CH₂ H H

H H H

TABLE 19 Present Compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 156 CF₂HCH₂H H

H H H 157 CF₃CF₂CH₂ H H

H H H 158 CF₂HCF₂CH₂ H H

H H H 159 CF₃CF₂CF₂CH₂ H H

H H H 160 CF₃CFHCF₂CH₂ H H

H H H 161 CF₂HCH₂ H H

H H H 162 CF₃CF₂CH₂ H H

H H H 163 CF₂HCF₂CH₂ H H

H H H 164 CF₃CF₂CF₂CH₂ H H

H H H 165 CF₃CFHCF₂CH₂ H H

H H H

TABLE 20 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 166 CF₂HCH₂H H

H H H 167 CF₃CF₂CH₂ H H

H H H 168 CF₂HCF₂CH₂ H H

H H H 169 CF₃CF₂CF₂CH₂ H H

H H H 170 CF₃CFHCF₂CH₂ H H

H H H 171 CF₂HCH₂ H H

H H H 172 CF₃CF₂CH₂ H H

H H H 173 CF₂HCF₂CH₂ H H

H H H 174 CF₃CF₂CF₂CH₂ H H

H H H 175 CF₃CFHCF₂CH₂ H H

H H H

TABLE 21 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 176 CF₂HCH₂H

H H H H 177 CF₃CF₂CH₂ H

H H H H 178 CF₂HCF₂CH₂ H

H H H H 179 CF₃CF₂CF₂CH₂ H

H H H H 180 CF₃CFHCF₂CH₂ H

H H H H 181 CF₂HCH₂ H

H H H H 182 CF₃CF₂CH₂ H

H H H H 183 CF₂HCF₂CH₂ H

H H H H 184 CF₃CF₂CF₂CH₂ H

H H H H 185 CF₃CFHCF₂CH₂ H

H H H H

TABLE 22 Present Compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 186 CF₂HCH₂H

H H H H 187 CF₃CF₂CH₂ H

H H H H 188 CF₂HCF₂CH₂ H

H H H H 189 CF₃CF₂CF₂CH₂ H

H H H H 190 CF₃CFHCF₂CH₂ H

H H H H 191 CF₂HCH₂ H

H H H H 192 CF₃CF₂CH₂ H

H H H H 193 CF₂HCF₂CH₂ H

H H H H 194 CF₃CF₂CF₂CH₂ H

H H H H 195 CF₃CFHCF₂CH₂ H

H H H H

TABLE 23 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 196 CF₂HCH₂H

H H H H 197 CF₃CF₂CH₂ H

H H H H 198 CF₂HCF₂CH₂ H

H H H H 199 CF₃CF₂CF₂CH₂ H

H H H H 200 CF₃CFHCF₂CH₂ H

H H H H 201 CF₂HCH₂ H

H H H H 202 CF₃CF₂CH₂ H

H H H H 203 CF₂HCF₂CH₂ H

H H H H 204 CF₃CF₂CF₂CH₂ H

H H H H 205 CF₃CFHCF₂CH₂ H

H H H H

TABLE 24 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 206 CF₂HCH₂H

H H H H 207 CF₃CF₂CH₂ H

H H H H 208 CF₂HCF₂CH₂ H

H H H H 209 CF₃CF₂CF₂CH₂ H

H H H H 210 CF₃CFHCF₂CH₂ H

H H H H 211 CF₂HCH₂ H

H H H H 212 CF₃CF₂CH₂ H

H H H H 213 CF₂HCF₂CH₂ H

H H H H 214 CF₃CF₂CF₂CH₂ H

H H H H 215 CF₃CFHCF₂CH₂ H

H H H H

TABLE 25 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 216 CF₂HCH₂H

H H H H 217 CF₃CF₂CH₂ H

H H H H 218 CF₂HCF₂CH₂ H

H H H H 219 CF₃CF₂CF₂CH₂ H

H H H H 220 CF₃CFHCF₂CH₂ H

H H H H 221 CF₂HCH₂ H

H H H H 222 CF₃CF₂CH₂ H

H H H H 223 CF₂HCF₂CH₂ H

H H H H 224 CF₃CF₂CF₂CH₂ H

H H H H 225 CF₃CFHCF₂CH₂ H

H H H H

TABLE 26 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 226 CF₂HCH₂H

H H H H 227 CF₃CF₂CH₂ H

H H H H 228 CF₂HCF₂CH₂ H

H H H H 229 CF₃CF₂CF₂CH₂ H

H H H H 230 CF₃CFHCF₂CH₂ H

H H H H 231 CF₂HCH₂ H

H H H H 232 CF₃CF₂CH₂ H

H H H H 233 CF₂HCF₂CH₂ H

H H H H 234 CF₃CF₂CF₂CH₂ H

H H H H 235 CF₃CFHCF₂CH₂ H

H H H H

TABLE 27 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 236 CF₂HCH₂H

H H H H 237 CF₃CF₂CH₂ H

H H H H 238 CF₂HCF₂CH₂ H

H H H H 239 CF₃CF₂CF₂CH₂ H

H H H H 240 CF₃CFHCF₂CH₂ H

H H H H 241 CF₂HCH₂ H

H H H H 242 CF₃CF₂CH₂ H

H H H H 243 CF₂HCF₂CH₂ H

H H H H 244 CF₃CF₂CF₂CH₂ H

H H H H 245 CF₃CFHCF₂CH₂ H

H H H H

TABLE 28 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 246 CF₂HCH₂H

H H H H 247 CF₃CF₂CH₂ H

H H H H 248 CF₂HCF₂CH₂ H

H H H H 249 CF₃CF₂CF₂CH₂ H

H H H H 250 CF₃CFHCF₂CH₂ H

H H H H 251 CF₂HCH₂ H

H H H H 252 CF₃CF₂CH₂ H

H H H H 253 CF₂HCF₂CH₂ H

H H H H 254 CF₃CF₂CF₂CH₂ H

H H H H 255 CF₃CFHCF₂CH₂ H

H H H H

TABLE 29 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 256 CF₂HCH₂H

H H H H 257 CF₃CF₂CH₂ H

H H H H 258 CF₂HCF₂CH₂ H

H H H H 259 CF₃CF₂CF₂CH₂ H

H H H H 260 CF₃CFHCF₂CH₂ H

H H H H 261 CF₂HCH₂ H

H H H H 262 CF₃CF₂CH₂ H

H H H H 263 CF₂HCF₂CH₂ H

H H H H 264 CF₃CF₂CF₂CH₂ H

H H H H 265 CF₃CFHCF₂CH₂ H

H H H H

TABLE 30 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 266 CF₂HCH₂H

H H H H 267 CF₂HCF₂CH₂ H

H H H H 268 CF₃CF₂CF₂CH₂ H

H H H H 269 CF₃CFHCF₂CH₂ H

H H H H 270 CF₂HCH₂ H

H H H H 271 CF₃CF₂CH₂ H

H H H H 272 CF₂HCF₂CH₂ H

H H H H 273 CF₃CF₂CF₂CH₂ H

H H H H 274 CF₃CFHCF₂CH₂ H

H H H H

TABLE 31 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 276 CF₂HCH₂H

H H H H 277 CF₃CF₂CH₂ H

H H H H 278 CF₂HCF₂CH₂ H

H H H H 279 CF₃CF₂CF₂CH₂ H

H H H H 280 CF₃CFHCF₂CH₂ H

H H H H 281 CF₂HCH₂ H

H H H H 282 CF₃CF₂CH₂ H

H H H H 283 CF₂HCF₂CH₂ H

H H H H 284 CF₃CF₂CF₂CH₂ H

H H H H 285 CF₃CFHCF₂CH₂ H

H H H H

TABLE 32 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 286 CF₂HCH₂H

H H H H 287 CF₃CF₂CH₂ H

H H H H 288 CF₂HCF₂CH₂ H

H H H H 289 CF₃CF₂CF₂CH₂ H

H H H H 290 CF₃CFHCF₂CH₂ H

H H H H 291 CF₂HCH₂ H

H H H H 292 CF₂HCF₂CH₂ H

H H H H 293 CF₃CF₂CF₂CH₂ H

H H H H 294 CF₃CFHCF₂CH₂ H

H H H H

TABLE 33 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 296 CF₂HCH₂H

H H H H 297 CF₃CF₂CH₂ H

H H H H 298 CF₂HCF₂CH₂ H

H H H H 299 CF₃CF₂CF₂CH₂ H

H H H H 300 CF₃CFHCF₂CH₂ H

H H H H 301 CF₂HCH₂ H

H H H H 302 CF₃CF₂CH₂ H

H H H H 303 CF₂HCF₂CH₂ H

H H H H 304 CF₃CF₂CF₂CH₂ H

H H H H 305 CF₃CFHCF₂CH₂ H

H H H H

TABLE 34 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 306 CF₂HCH₂H

H H H H 307 CF₃CF₂CH₂ H

H H H H 308 CF₂HCF₂CH₂ H

H H H H 309 CF₃CF₂CF₂CH₂ H

H H H H 310 CF₃CFHCF₂CH₂ H

H H H H

TABLE 35 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 311 CF₂HCH₂H OCH₃ H H H H 312 CF₂HCF₂CH₂ H OCH₃ H H H H 313 CF₃CF₂CF₂CH₂ H OCH₃ H HH H 314 CF₃CFHCF₂CH₂ H OCH₃ H H H H 315 CF₂HCH₂ H OCH₂CH₃ H H H H 316CF₃CF₂CH₂ H OCH₂CH₃ H H H H 317 CF₂HCF₂CH₂ H OCH₂CH₃ H H H H 318CF₃CF₂CF₂CH₂ H OCH₂CH₃ H H H H 319 CF₃CFHCF₂CH₂ H OCH₂CH₃ H H H H 320CF₂HCH₂ H OCH(CH₃)₂ H H H H 321 CF₃CF₂CH₂ H OCH(CH₃)₂ H H H H 322CF₂HCF₂CH₂ H OCH(CH₃)₂ H H H H 323 CF₃CF₂CF₂CH₂ H OCH(CH₃)₂ H H H H 324CF₃CFHCF₂CH₂ H OCH(CH₃)₂ H H H H 325 CF₂HCH₂ H OCH₂CH₂N(CH₃)₂ H H H H326 CF₃CF₂CH₂ H OCH₂CH₂N(CH₃)₂ H H H H 327 CF₂HCF₂CH₂ H OCH₂CH₂N(CH₃)₂ HH H H 328 CF₃CF₂CF₂CH₂ H OCH₂CH₂N(CH₃)₂ H H H H 329 CF₃CFHCF₂CH₂ HOCH₂CH₂N(CH₃)₂ H H H H 330 CF₂HCH₂ H OCH₂CF₃ H H H H 331 CF₃CF₂CH₂ HOCH₂CF₃ H H H H 332 CF₂HCF₂CH₂ H OCH₂CF₃ H H H H 333 CF₃CF₂CF₂CH₂ HOCH₂CF₃ H H H H 334 CF₃CFHCF₂CH₂ H OCH₂CF₃ H H H H

TABLE 36 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 335 CF₂HCH₂H OCH₂CF₃ H H H H 336 CF₃CF₂CH₂ H OCH₂CF₃ H H H H 337 CF₂HCF₂CH₂ HOCH₂CF₃ H H H H 338 CF₃CF₂CF₂CH₂ H OCH₂CF₃ H H H H 339 CF₃CFHCF₂CH₂ HOCH₂CF₃ H H H H 340 CF₂HCH₂ H OCH₂CF₂CF₂H H H H H 341 CF₃CF₂CH₂ HOCH₂CF₂CF₂H H H H H 342 CF₂HCF₂CH₂ H OCH₂CF₂CF₂H H H H H 343CF₃CF₂CF₂CH₂ H OCH₂CF₂CF₂H H H H H 344 CF₃CFHCF₂CH₂ H OCH₂CF₂CF₂H H H HH 345 CF₂HCH₂ H OCH₂CF₂CF₃ H H H H 346 CF₃CF₂CH₂ H OCH₂CF₂CF₃ H H H H347 CF₂HCF₂CH₂ H OCH₂CF₂CF₃ H H H H 348 CF₃CF₂CF₂CH₂ H OCH₂CF₂CF₃ H H HH 349 CF₃CFHCF₂CH₂ H OCH₂CF₂CF₃ H H H H 350 CF₂HCH₂ H NHC(O)CH₃ H H H H351 CF₃CF₂CH₂ H NHC(O)CH₃ H H H H 352 CF₂HCF₂CH₂ H NHC(O)CH₃ H H H H 353CF₃CF₂CF₂CH₂ H NHC(O)CH₃ H H H H 354 CF₃CFHCF₂CH₂ H NHC(O)CH₃ H H H H355 CF₂HCH₂ H NHC(O)CH₂CH₃ H H H H 356 CF₃CF₂CH₂ H NHC(O)CH₂CH₃ H H H H357 CF₂HCF₂CH₂ H NHC(O)CH₂CH₃ H H H H 358 CF₃CF₂CF₂CH₂ H NHC(O)CH₂CH₃ HH H H 359 CF₃CFHCF₂CH₂ H NHC(O)CH₂CH₃ H H H H

TABLE 37 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 360 CF₂HCH₂H

H H H H 361 CF₂HCF₂CH₂ H

H H H H 362 CF₃CF₂CF₂CH₂ H

H H H H 363 CF₃CFHCF₂CH₂ H

H H H H 364 CF₂HCH₂ H

H H H H 365 CF₃CF₂CH₂ H

H H H H 366 CF₂HCF₂CH₂ H

H H H H 367 CF₃CF₂CF₂CH₂ H

H H H H 368 CF₃CFHCF₂CH₂ H

H H H H

TABLE 38 Present compound R¹⁰⁰ R³⁰¹ R³⁰² R³⁰³ R⁶⁰¹ R⁶⁰² R⁶⁰³ 369 CF₂HCH₂H NHC(O)OCH₃ H H H H 370 CF₃CF₂CH₂ H NHC(O)OCH₃ H H H H 371 CF₂HCF₂CH₂ HNHC(O)OCH₃ H H H H 372 CF₃CF₂CF₂CH₂ H NHC(O)OCH₃ H H H H 373CF₃CFHCF₂CH₂ H NHC(O)OCH₃ H H H H 374 CF₂HCH₂ H NHC(O)OCH₂CH₃ H H H H375 CF₃CF₂CH₂ H NHC(O)OCH₂CH₃ H H H H 376 CF₂HCF₂CH₂ H NHC(O)OCH₂CH₃ H HH H 377 CF₃CF₂CF₂CH₂ H NHC(O)OCH₂CH₃ H H H H 378 CF₃CFHCF₂CH₂ HNHC(O)OCH₂CH₃ H H H H 379 CF₂HCH₂ H OCH₂CH₂CH₃ H H H H 380 CF₃CF₂CH₂ HOCH₂CH₂CH₃ H H H H 381 CF₂HCF₂CH₂ H OCH₂CH₂CH₃ H H H H 382 CF₃CF₂CF₂CH₂H OCH₂CH₂CH₃ H H H H 383 CF₃CFHCF₂CH₂ H OCH₂CH₂CH₃ H H H H

Next, the Formulation examples of the Present compound are shown below.The “part(s)” represents “part(s) by weight” unless otherwise specified.

Formulation Example 1

Any one of the Present compounds 1 to 383 (10 parts) is mixed with amixture of xylene (35 parts) and DMF (35 parts), and thenpolyoxyethylene styryl phenyl ether (14 parts) and calciumdodecylbenzene sulfonate (6 parts) are added thereto, followed by mixingthem to obtain each formulation.

Formulation Example 2

Sodium lauryl sulfate (4 parts), calcium lignin sulfonate (2 parts),synthetic hydrated silicon oxide fine powder (20 parts), anddiatomaceous earth (54 parts) are mixed, and further any one of thePresent compounds 1 to 383 (20 parts) is added thereto, followed bymixing them to obtain each wettable powder.

Formulation Example 3

To any one of the Present compounds 1 to 383 (2 parts) are addedsynthetic hydrated silicon oxide fine powder (1 part), calcium ligninsulfonate (2 parts), bentonite (30 parts), and kaolin clay (65 parts),followed by mixing them to obtain a mixture. To the mixture is thenadded an appropriate amount of water, and the resulting mixture isadditionally stirred, and subjected to granulation with a granulator andforced-air drying to obtain each granular formulation.

Formulation Example 4

Any one of the Present compounds 1 to 383 (1 part) is mixed with anappropriate amount of acetone, and then synthetic hydrated silicon oxidefine powder (5 parts), isopropyl acid phosphate (0.3 parts), and kaolinclay (93.7 parts) are added thereto, followed by mixing with stirringthoroughly and removal of acetone from the mixture by evaporation toobtain each powder formulation.

Formulation Example 5

A mixture of polyoxyethylene alkyl ether sulfate ammonium salt and whitecarbon (weight ratio of 1:1) (35 parts), any one of the Presentcompounds 1 to 383 (10 parts), and water (55 parts) are mixed, followedby finely grounding by a wet grinding method to obtain each flowableformulation.

Formulation Example 6

Any one of the Present compounds 1 to 383 (0.1 part) is mixed with amixture of xylene (5 parts) and trichloroethane (5 parts), and theresulting mixture is then mixed with kerosene (89.9 parts) to obtaineach oil solution.

Formulation Example 7

Any one of the Present compounds 1 to 383 (10 mg) is mixed with acetone(0.5 mL), and the solution is added dropwise to a solid feed powder foran animal (solid feed powder for rearing and breeding CE-2, manufacturedby CLEA Japan, Inc.) (5 g), followed by mixing the resulting mixtureuniformly, and then by drying it by evaporation of acetone to obtaineach poison bait.

Formulation Example 8

Any one of the Present compounds 1 to 383 (0.1 part) and Neothiozole(manufactured by Chuo Kasei Co., Ltd.) (49.9 parts) are placed into anaerosol can. After mounting an aerosol valve, dimethyl ether (25 parts)and LPG (25 parts) are filled, followed by shaking and further mountingan actuator to obtain each oily aerosol.

Formulation Example 9

A mixture of any one of the Present compounds 1 to 383 (0.6 parts), BHT(2,6-di-tert-butyl-4-methylphenol) (0.01 part), xylene (5 parts),deodorized kerosene (3.39 parts), and an emulsifier {Rheodol MO-60(manufactured by Kao Corporation)} (1 part), and distilled water (50parts) are filled into an aerosol container, and a valve part isattached. Then, a propellant (LPG) (40 parts) is filled therein throughthe valve under pressure to obtain each aqueous aerosol.

Formulation Example 10

Any one of the Present compounds 1 to 383 (0.1 g) is mixed withpropylene glycol (2 mL), and the resulting solution is impregnated intoa ceramic plate having a size of 4.0 cm×4.0 cm and a thickness of 1.2 cmto obtain each thermal fumigant.

Formulation Example 11

Any one of the Present compounds 1 to 383 (5 parts) and ethylene-methylmethacrylate copolymer (the ratio of the methyl methacrylate in thecopolymer: 10% by weight, Acryft (registered trademark) WD 301,manufactured by Sumitomo Chemical Co. Ltd.) (95 parts) are melted andkneaded with a closed type pressure kneader (manufactured by MoriyamaCo., Ltd.), and the resulting kneaded product is extruded from anextrusion molding machine through a molding die to obtain eachrod-shaped molded product having a length of 15 cm and a diameter of 3mm.

Formulation Example 12

Any one of the Present compounds 1 to 383 (5 parts) and flexible vinylchloride resin (95 parts) are melted and kneaded with a closed typepressure kneader (manufactured by Moriyama Co., Ltd.), and the resultingkneaded product is extruded from an extrusion molding machine through amolding die to obtain each rod-shaped molded product having a length of15 cm and a diameter of 3 mm.

Formulation Example 13

Any one of the Present compounds 1 to 383 (100 mg), lactose (68.75 mg),corn starch (237.5 mg), microcrystalline cellulose (43.75 mg),polyvinylpyrrolidone (18.75 mg), sodium carboxymethyl starch (28.75 mg),and magnesium stearate (2.5 mg) are mixed, and the resulting mixture iscompressed to an appropriate size to obtain each tablet.

Formulation Example 14

Any one of the Present compounds 1 to 383 (25 mg), lactose (60 mg), cornstarch (25 mg), carmellose calcium (6 mg), and an appropriate amount of5% hydroxypropyl methylcellulose are mixed, and the resulting mixture isfilled into a hard shell gelatin capsule or a hydroxypropylmethylcellulose capsule to obtain each capsule.

Formulation Example 15

To any one of the Present compounds 1 to 383 (100 mg), fumaric acid (500mg), sodium chloride (2,000 mg), methylparaben (150 mg), propylparaben(50 mg), granulated sugar (25,000 mg), sorbitol (70% solution) (13,000mg), Veegum K (manufactured by Vanderbilt Co.) (100 mg), perfume (35mg), and a coloring agent (500 mg) is added distilled water so that thefinal volume is set to be 100 mL, followed by mixing them to obtain eachsuspension for oral administration.

Formulation Example 16

Any one of the Present compounds 1 to 383 (5% by weight) is mixed withan emulsifier (5% by weight), benzyl alcohol (3% by weight), andpropylene glycol (30% by weight), and phosphate buffer is added theretoso that the pH of the solution is set to be 6.0 to 6.5, and then wateris added thereto as the rest parts to obtain each solution for oraladministration.

Formulation Example 17

To a mixture of fractional distillated palm oil (57% by weight) andpolysorbate 85 (3% by weight) is added aluminum distearate (5% byweight), and the mixture is dispersed by heating. The resulting mixtureis cooled to room temperature, and saccharin (25% by weight) isdispersed in the oil vehicle. Any one of the Present compounds 1 to 383(10% by weight) is divided thereto to obtain each paste formulation fororal administration.

Formulation Example 18

Any one of the Present compounds 1 to 383 (5% by weight) is mixed with alimestone filler (95% by weight), followed by a wet granulation of theresulting mixture to obtain each granule for oral administration.

Formulation Example 19

Any one of the Present compounds 1 to 383 (5 parts) is mixed withdiethylene glycol monoethyl ether (80 parts), and propylene carbonate(15 parts) is added thereto, and the resulting mixture is mixed toobtain each spot-on solution.

Formulation Example 20

Any one of the Present compounds 1 to 383 (10 parts) is mixed withdiethylene glycol monoethyl ether (70 parts), and 2-octyldodecanol (20parts) is added thereto, and the resulting mixture is mixed to obtaineach pour-on solution.

Formulation Example 21

To any one of the Present compounds 1 to 383 (0.5 parts) are addedNikkol (registered trademark) TEALS-42 (manufactured by Nikko ChemicalsCo., Ltd.: a 42% triethanolamine lauryl sulfate aqueous solution) (60parts) and propylene glycol (20 parts), and the resulting mixture ismixed with stirring thoroughly to obtain a homogeneous solution, andwater (19.5 parts) is then added thereto and the resulting mixture isfurther mixed with stirring thoroughly to obtain each homogeneoussolution of shampoo formulation.

Formulation Example 22

Any one of the Present compounds 1 to 383 (0.15% by weight), animal feed(95% by weight), and a mixture (4.85% by weight) consisting of dibasiccalcium phosphate, diatomaceous earth, Aerosil, and carbonate (or chalk)are mixed with stirring thoroughly to obtain each premix for animalfeed.

Formulation Example 23

Any one of the Present compounds 1 to 383 (7.2 g) and Hosco (registeredtrademark) S-55 (manufactured by Maruishi Pharmaceuticals) (92.8 g) aremixed at 100° C., and the resulting mixture is poured into a suppositorymold, followed by performing a cooling solidification to obtain eachsuppository.

Next, Test examples are used to show efficacies of the Present compoundson controlling harmful arthropods. In the following Test examples, thetests were carried out at 25° C.

Test Example 1

Each test compound is formulated according to the process described inthe Formulation example 5 to obtain each formulation, and watercontaining a spreader (0.03% by volume) is added thereto to prepare adiluted solution containing a prescribed concentration of each testcompound.

Cucumber (Cucumis sativus) seedlings (on the developmental stage of thesecond true leaf) are planted in a plastic cup and approximately 30heads of cotton aphid (Aphis gossypii) (all stages of life) are releasedonto the cucumber seedlings. After 1 day, each of said diluted solutionsis sprayed into the seedlings in a ratio of 10 mL/seedling. Afteradditional 5 days, the number of the surviving insects is examined andthe controlling value is calculated by the following equation.

Controlling value(%)={1−(Cb×Tai)/(Cai×Tb)}×100

wherein the symbols in the formula represent the following meanings.

Cb: Number of the test insects in untreated group;

Cai: Number of the surviving insects at the time of the investigation inuntreated group;

Tb: Number of the test insects in treated group;

Tai: Number of the surviving insects at the time of the investigation intreated group;

Here the “untreated group” represents a group where a similar treatmentprocedure to that of the treated group except not using each testcompound is done.

The results of the test that was carried out according to the Testexample 1 are shown below.

When the prescribed concentration was 500 ppm, each of the followingPresent compounds used as a test compound showed 90% or greater as thecontrolling value.

Present compound number: 1, 2, 3, 5, 6, 7, 8, 9, 11, 13, 14, 21, 22, 23,25, 28, 31, 32, 33, 34, 36, 37, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49,50, 51, 52, 53, 54, 55, 56, 58, 57, 59, 60, 61, 62, 63, 64, 65, 66, 67,and 68

The results of the test that was carried out according to the Testexample 1 are shown below.

When the prescribed concentration was 200 ppm, each of the followingPresent compounds used as a test compound showed 90% or greater as thecontrolling value.

Present compound number: 1, 2, 5, 6, 8, 11, 44, 46, 52, 56, 58, 59, 60,61, 62, 64, 65, 66, 67, and 68

Test Example 2

Each test compound is formulated according to the process described inthe Formulation example 5 to obtain each formulation, and water is addedthereto to prepare a diluted solution containing a prescribedconcentration of each test compound.

Cucumber seedlings (on the developmental stage of the second true leaf)are planted in a plastic cup, and each of the diluted solutions isirrigated into the plant foot in a ratio of 5 mL/seedling. After 7 days,approximately 30 heads of cotton aphid (Aphis gossypii) (all stages oflife) are inoculated onto the leaves of the seedlings. After additional6 days, the number of the surviving insects is examined and thecontrolling value is calculated by the following equation.

Controlling value(%)={1−(Cb×Tai)/(Cai×Tb)}×100

wherein the symbols in the formula represent the following meanings.

Cb: Number of the test insects in untreated group;

Cai: Number of the surviving insects at the time of the investigation inuntreated group;

Tb: Number of the test insects in treated group;

Tai: Number of the surviving insects at the time of the investigation intreated group;

Here the “untreated group” represents a group where a similar treatmentprocedure to that of the treated group except not using each testcompound is done.

The results of the test that was carried out according to the Testexample 2 are shown below.

When the prescribed concentration was 200 ppm, each of the followingPresent compounds used as a test compound showed 90% or greater as thecontrolling value.

Present compound number: 60, 66, and 67

Test Example 3

Each test compound is formulated according to the process described inthe Formulation example 5 to obtain each formulation, and watercontaining a spreader (0.03% by volume) is added thereto to prepare adiluted solution containing a prescribed concentration of each testcompound.

Rice (Oryza sativa) seedlings (on the developmental stage of the secondtrue leaf) are planted in a plastic cup, and each of the dilutedsolutions is sprayed into the seedlings in a ratio of 10 mL/seedling.Thereafter, 20 heads of the 3rd instar larvae of brown planthopper(Nilaparvata lugens) are released onto the rice seedlings. After 6 days,the number of the surviving insects is examined and the mortality ofinsects is calculated by the following equation.

Mortality of insects(%)={1−Number of surviving insects/20}×100

The results of the test that was carried out according to the Testexample 3 are shown below.

When the prescribed concentration was 500 ppm, each of the followingPresent compounds used as a test compound showed 90% or greater as themortality of insects. Present compound number: 1, 6, 8, 25, 28, 47, and64

Test Example 4

Each test compound is formulated according to the process described inthe Formulation example 5 to obtain each formulation, and water is addedthereto to prepare a diluted solution containing a prescribedconcentration of each test compound.

Each of the diluted solutions (5 mL) is added to a plastic cup, andtherein is installed rice seedlings (on the developmental stage of thesecond true leaf) planted in a plastic cup having a hole in the bottom.After 7 days, 20 heads of the 3rd instar larvae of brown planthopper(Nilaparvata lugens) are released onto the rice seedlings. Afteradditional 6 days, the number of the surviving insects is examined andthe mortality of insects is calculated by the following equation.

Mortality of insects(%)={1−Number of surviving insects/20}×100

Test Example 5

Each test compound is formulated according to the process described inthe Formulation example 5 to obtain each formulation, and water is addedthereto to prepare a diluted solution containing a prescribedconcentration of each test compound.

An artificial diet (Insecta LF, manufactured by Nosan Corporation) (7.7g) is placed in a plastic cup, and each of the diluted solutions (2 mL)is irrigated thereto. Five (5) heads of the 4th instar larvae of tobaccocutworm (Spodoptera litura) are released onto the artificial diet, andthe cup is covered with a lid. After 5 days, the number of the survivinginsects is counted, and the mortality of insects is calculated by thefollowing equation.

Mortality of insects(%)=(1−Number of surviving insects/5)×100

The results of the test that was carried out according to the Testexample 5 are shown below.

When the prescribed concentration was 500 ppm, each of the followingPresent compounds used as a test compound showed 80% or greater as themortality of insects. Present compound number: 7, 8, 9, 11, 13, 14, 22,23, 41, 47, 48, 49, 54, 56, 57, 58, 67, 68, and 69

Test Example 6

Each test compound is formulated according to the process described inthe Formulation example 5 to obtain each formulation, and watercontaining a spreader (0.03% by volume) is added thereto to prepare adiluted solution containing a prescribed concentration of each testcompound.

Cabbage (Brassicae oleracea) seedlings (on the developmental stage ofthe second to third true leaf) are planted in a plastic cup, and each ofthe diluted solutions is sprayed into the seedlings in a ratio of 20mL/seedling. Thereafter, the stem and leaf of the seedling are cut out,and placed into a plastic cup lined with a filter paper. Five (5) headsof the 2nd instar larvae of cabbage moth (Plutella xylostella) arereleased into the cup, and the cup is covered with a lid. After 5 days,the number of the surviving insects is counted, and the mortality ofinsects is calculated by the following equation.

Mortality %=(1−Number of surviving insects/5)×100

The results of the test that was carried out according to the Testexample 6 are shown below.

When the prescribed concentration was 500 ppm, each of the followingPresent compounds used as a test compound showed 80% or greater as themortality of insects. Present compound number: 1, 2, 3, 5, 6, 7, 8, 9,11, 13, 14, 18, 19, 20, 21, 22, 23, 25, 26, 27, 28, 32, 33, 34, 40, 41,42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 56, 55, 57, 58, 59,60, 61, 62, 63, 64, 65, 66, 67, 68, and 69

Test Example 7

Each test compound is formulated according to the process described inthe Formulation example 5 to obtain each formulation, and watercontaining a spreader (0.03% by volume) is added thereto to prepare adiluted solution containing a prescribed concentration of each testcompound.

Cabbage seedlings (on the developmental stage of the third to fourthtrue leaf) are planted in a plastic cup, and each of the dilutedsolutions is sprayed into the seedlings in a ratio of 20 mL/seedling.Thereafter, 10 heads of the 3rd instar larvae of cabbage moth (Plutellaxylostella) are released into the cabbage seedlings, and held in aplastic container covered with a net. After 5 days, the number of thesurviving insects is counted, and the mortality of insects is calculatedby the following equation.

Mortality %=(1−Number of surviving insects/10)×100

The results of the test that was carried out according to the Testexample 7 are shown below.

When the prescribed concentration was 200 ppm, each of the followingPresent compounds used as a test compound showed 90% or greater as themortality of insects.

Present compound number: 2, 5, 6, 7, 8, 9, 11, 18, 27, 32, 33, 34, 32,33, 34, 41, 47, 48, 49, 55, 56, 57, 58, 59, 60, 62, 63, 64, 65, 66, 67,68, 69, and 70

Test Example 8

Each test compound is dissolved into a mixed solution (50 μL) ofpolyoxyethylene sorbitan mono-cocoate:acetone (at a volume ratio ofpolyoxyethylene sorbitan mono-cocoate:acetone=5:95) per 1 mg of the testcompound, and water containing a spreader (0.03% by volume) is addedthereto to prepare a diluted solution containing a prescribedconcentration of each test compound.

Seeds of corns (Zea mays) are inoculated onto a tray lined with wetKimwipes. After the corns are grown for 5 days, the entire seedlings ofthe corns are immersed into each of the diluted solutions for 30seconds. Thereafter, two seedlings are placed into each plastic petridish (diameter: 90 mm), and 10 heads of the 2nd instar larvae of westerncorn rootworm (Diabrotica virgifera virgifera) are released into thedish, and the dish is covered with a lid. After 5 days, the number ofthe dead insects is counted, and the mortality of insects is calculatedby the following equation.

Mortality of insects(%)=(Number of dead insects/10)×100

The results of the test that was carried out according to the Testexample 8 are shown below.

When the prescribed concentration was 500 ppm, each of the followingPresent compounds used as a test compound showed 80% or greater as themortality of insects.

Present compound number: 1, 2, 3, 5, 6, 9, 11, 20, 26, 27, 31, 32, 33,34, 41, 42, 48, 49, 56, 57, 58, 59, 60, and 64

Test Example 9

Each test compound is dissolved into a mixed solution (10 μL) of xylene,DMF, and a surfactant (at a volume ratio of xylene:DMF:surfactant=4:4:1)per 1 mg of the test compound, and water containing a spreader (0.03% byvolume) is added thereto to prepare a diluted solution containing aprescribed concentration of each test compound.

Cucumber seedlings (on the developmental stage of the second to thirdtrue leaf) are planted in a plastic cup, and each of the dilutedsolutions is sprayed into the seedlings in the ratio of 10 mL/seedling.Thereafter, the second leaves are cut out and placed into a plastic cup,and 10 heads of the 2nd instar larvae of cucurbit leaf beetle(Aulacophora femoralis) are released into the cup, and the cup iscovered with a lid. After 5 days, the number of the dead insects iscounted, and the mortality of insects is calculated by the followingequation.

Mortality of insects(%)=(Number of dead insects/10)×100

The results of the test that was carried out according to the Testexample 9 are shown below.

When the prescribed concentration was 50 ppm, each of the followingPresent compounds used as a test compound showed 80% or greater as themortality of insects. Present compound number: 7, 8, and 9

Test Example 10

Each test compound is formulated according to the process described inthe Formulation example 5 to obtain each formulation, and water is addedthereto to prepare a diluted solution containing a prescribedconcentration of each test compound.

A bottom of a plastic cup having a diameter of 5.5 cm is lined with thesame size of a filter paper, and each of the diluted solutions (0.7 mL)is added dropwise on the filter paper, and sucrose (30 mg) ishomogeneously placed into the plastic cup as a bait. Ten (10) heads offemale adult housefly (Musca domestica) are released into the plasticcup, and the cup is covered with a lid. After 24 hours, life or death ofthe housefly is examined and the mortality of insects is calculated bythe following equation.

Mortality of insects(%)=(Number of dead insects/Number of testinsects)×100

The results of the test that was carried out according to the Testexample 10 are shown below.

When the prescribed concentration was 500 ppm, each of the followingPresent compounds used as a test compound showed 100% or greater as themortality of insects. Present compound number: 5, 6, 13, 14, 32, 66, and67

INDUSTRIAL APPLICABILITY

The Present compounds have excellent control efficacies against harmfularthropods.

1. A compound represented by formula (I) or an N-oxide thereof:

wherein: R¹ represents a C2-C10 chain hydrocarbon group having one ormore halogen atoms, a (C1-C5 alkoxy)C2-C5 alkyl group having one or morehalogen atoms, a (C1-C5 alkylsulfanyl)C2-C5 alkyl group having one ormore halogen atoms, a (C1-C5 alkylsulfinyl)C2-C5 alkyl group having oneor more halogen atoms, a (C1-C5 alkylsulfonyl)C2-C5 alkyl group havingone or more halogen atoms, a (C3-C7 cycloalkyl)C1-C3 alkyl group havingone or more substituents selected from Group G, or a C3-C7 cycloalkylgroup having one or more substituents selected from Group G; R²represents a C1-C6 alkyl group optionally having one or more halogenatoms, a cyclopropylmethyl group, or a cyclopropyl group; q represents0, 1, 2, 3, or 4; R³ represents a C1-C6 chain hydrocarbon groupoptionally having one or more substituents selected from Group B, aphenyl group optionally having one or more substituents selected fromGroup D, a 5 or 6 membered aromatic heterocyclic group optionally havingone or more substituents selected from Group D, a OR¹², a NR¹¹R¹², aNR^(11a)R^(12a), a NR²⁹NR¹¹R¹², a NR²⁹OR¹¹, a NR¹¹C(O)R¹³, aNR²⁹NR¹¹C(O)R¹³, a NR¹¹C(O)OR¹⁴, a NR²⁹NR¹¹C(O)OR¹⁴, a NR¹¹C(O)NR¹⁵R¹⁶,a NR²⁴NR¹¹C(O)NR¹⁵R¹⁶, a N═CHNR¹⁵R¹⁶, a N═S(O)_(x)R¹⁵R¹⁶, a S(O)_(y)R¹⁵,a SF₅, a C(O)OR¹⁷, a C(O)NR¹¹R¹², a cyano group, a nitro group, or ahalogen atom, wherein when q represents 2 or 3, two or three R³ may beidentical to or different from each other; p represents 0, 1, 2, or 3;R⁶ represents a C1-C6 alkyl group optionally having one or more halogenatoms, a OR¹⁸, a NR¹⁸R¹⁹, a cyano group, a nitro group, or a halogenatom, wherein when p represents 2, two R⁶ may be identical to ordifferent from each other; R¹¹, R¹⁷, R¹⁸, R¹⁹, R²⁴, and R²⁹ representeach independently a hydrogen atom or a C1-C6 chain hydrocarbon groupoptionally having one or more halogen atoms; R¹² represents a hydrogenatom, a C1-C6 chain hydrocarbon group optionally having one or morehalogen atoms, a C1-C6 alkyl group having one substituent selected fromGroup F, or a S(O)₂R²³; R²³ represents a C1-C6 chain hydrocarbon groupoptionally having one or more halogen atoms or a phenyl group optionallyhaving one or more substituents selected from Group D; R^(11a) andR^(12a) are combined with the nitrogen atom to which they are attachedto represent a 3-7 membered nonaromatic heterocyclic group optionallyhaving one or more substituents selected from Group E, wherein the 3-7membered nonaromatic heterocyclic group represents an aziridine ring, anazetidine ring, a pyrrolidine ring, an imidazoline ring, animidazolidine ring, a piperidine ring, a tetrahydropyrimidine ring, ahexahydropyrimidine ring, a piperazine ring, an azepane ring, anoxazolidine ring, an isoxazolidine ring, a 1,3-oxazinane ring, amorpholine ring, a 1,4-oxazepane ring, a thiazolidine ring, anisothiazolidine ring, a 1,3-thiazinane ring, a thiomorpholine ring, or a1,4-thiazepane ring; R¹³ represents a hydrogen atom, a C1-C6 chainhydrocarbon group optionally having one or more halogen atoms, a C3-C7cycloalkyl group optionally having one or more halogen atoms, a (C3-C6cycloalkyl)C1-C3 alkyl group optionally having one or more halogenatoms, a phenyl group optionally having one or more substituentsselected from Group D, or a 5 or 6 membered aromatic heterocyclic groupoptionally having one or more substituents selected from Group D; R¹⁴represents a C1-C6 chain hydrocarbon group optionally having one or morehalogen atoms, a C3-C7 cycloalkyl group optionally having one or morehalogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group optionally havingone or more halogen atoms, or a phenyl C1-C3 alkyl group, wherein thephenyl moiety in the phenyl C1-C3 alkyl group may optionally have one ormore substituents selected from Group D; R¹⁵ and R¹⁶ represent eachindependently a C1-C6 alkyl group optionally having one or more halogenatoms; n and y represent each independently 0, 1, or 2; x represents 0or 1; Group B is selected from the group consisting of a C1-C6 alkoxygroup optionally having one or more halogen atoms, a C3-C6 alkenyloxygroup optionally having one or more halogen atoms, a C3-C6 alkynyloxygroup optionally having one or more halogen atoms, a C1-C6 alkylsulfanylgroup optionally having one or more halogen atoms, a C1-C6 alkylsulfinylgroup optionally having one or more halogen atoms, a C1-C6 alkylsulfonylgroup optionally having one or more halogen atoms, a C3-C6 cycloalkylgroup optionally having one or more halogen atoms, a cyano group, ahydroxy group, and a halogen atom; Group C is selected from the groupconsisting of a C1-C6 chain hydrocarbon group optionally having one ormore halogen atoms, a C1-C6 alkoxy group optionally having one or morehalogen atoms, a C3-C6 alkenyloxy group optionally having one or morehalogen atoms, a C3-C6 alkynyloxy group optionally having one or morehalogen atoms, and a halogen atom; Group D is selected from the groupconsisting of a C1-C6 chain hydrocarbon group optionally having one ormore halogen atoms, a hydroxy group, a C1-C6 alkoxy group optionallyhaving one or more halogen atoms, a C3-C6 alkenyloxy group optionallyhaving one or more halogen atoms, a C3-C6 alkynyloxy group optionallyhaving one or more halogen atoms, a sulfanyl group, a C1-C6alkylsulfanyl group optionally having one or more halogen atoms, a C1-C6alkylsulfinyl group optionally having one or more halogen atoms, a C1-C6alkylsulfonyl group optionally having one or more halogen atoms, anamino group, a NHR²¹, a NR²¹R²², a C(O)R²¹ group, a OC(O)R²¹ group, aC(O)OR²¹ group, a cyano group, a nitro group, and a halogen atom,wherein R²¹ and R²² represent each independently a C1-C6 alkyl groupoptionally having one or more halogen atoms; Group E is selected fromthe group consisting of a C1-C6 chain hydrocarbon group optionallyhaving one or more halogen atoms, a C1-C6 alkoxy group optionally havingone or more halogen atoms, a C3-C6 alkenyloxy group optionally havingone or more halogen atoms, a C3-C6 alkynyloxy group optionally havingone or more halogen atoms, a halogen atom, an oxo group, a hydroxygroup, a cyano group, and a nitro group; Group F is selected from thegroup consisting of a C1-C6 alkoxy group optionally having one or morehalogen atoms, an amino group, a NHR²¹, a NR²¹R²², a cyano group, aphenyl group optionally having one or more substituents selected fromGroup D, a 5 or 6 membered aromatic heterocyclic group optionally havingone or more substituents selected from Group D, a C3-C7 cycloalkyl groupoptionally having one or more halogen atoms, and a 3-7 memberednonaromatic heterocyclic group optionally having one or moresubstituents selected from Group C; and Group G is selected from thegroup consisting of a halogen atom and a C1-C6 haloalkyl group.
 2. Thecompound according to claim 1, wherein q represents 0, 1, or 2; and R³represents a C1-C6 chain hydrocarbon group optionally having one or moresubstituents selected from Group B, a phenyl group optionally having oneor more substituents selected from Group D, a 5 or 6 membered aromaticheterocyclic group optionally having one or more substituents selectedfrom Group D, a OR¹², a NR¹¹R¹², a NR^(11a)R^(12a), a NR¹¹C(O)R¹³, aNR²⁹NR¹¹C(O)R¹³, a NR¹¹C(O)OR¹⁴, a C(O)OR¹⁷, a C(O)NR¹¹R¹², a cyanogroup, a nitro group, or a halogen atom.
 3. The compound according toclaim 1, wherein q represents 0, 1, or 2; R³ represents a C1-C6 alkylgroup having one or more halogen atoms, a OR¹², or a halogen atom; andR¹² represents a hydrogen atom or a C1-C3 alkyl group optionally havingone or more halogen atoms.
 4. The compound according to claim 1, whereinp represents 0 or 1; and R⁶ represents a C1-C6 alkyl group optionallyhaving one or more halogen atoms, or a halogen atom.
 5. The compoundaccording to claim 1, wherein p represents
 0. 6. The compound accordingto claim 1, wherein R¹ represents a C2-C10 haloalkyl group.
 7. Thecompound according to claim 1, wherein R¹ represents a C3-C5 alkyl grouphaving four or more fluorine atoms.
 8. The compound according to claim1, wherein R² represents a C1-C6 alkyl group optionally having one ormore halogen atoms.
 9. The compound according to claim 1, wherein R²represents an ethyl group.
 10. The compound according to claim 1,wherein R¹ represents a C2-C10 haloalkyl group; R² represents an ethylgroup; q represents 0 or 1; R³ represents a C1-C6 alkyl group optionallyhaving one or more halogen atoms, or a halogen atom; p represents 0 or1; and R⁶ represents a C1-C6 alkyl group optionally having one or morehalogen atoms, or a halogen atom.
 11. The compound according to claim 1,wherein R¹ represents a C3-C5 alkyl group having four or more fluorineatoms; R² represents an ethyl group; q represents 0 or 1; R³ representsa C1-C6 alkyl group optionally having one or more halogen atoms, or ahalogen atom; and p represents
 0. 12. A composition for controlling aharmful arthropod comprising the compound according to claim 1 and aninert carrier.
 13. A method for controlling a harmful arthropod whichcomprises applying an effective amount of the compound according toclaim 1 to a harmful arthropod or a habitat where a harmful arthropodlives.